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Topic: Synthesis of 2-Bromo-1-PhenylEthanol  (Read 14472 times)

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Offline lutesium

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Synthesis of 2-Bromo-1-PhenylEthanol
« on: January 25, 2008, 07:59:36 PM »
How can this reagent be synthesised? I can't find it anywhere so we have to synthesise it but how??? Would a reduction of acetophenone then bromination work?

Thanx


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Offline sjh9

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #1 on: January 25, 2008, 08:59:38 PM »
How can this reagent be synthesised? I can't find it anywhere so we have to synthesise it but how??? Would a reduction of acetophenone then bromination work?

Thanx


Lutesium...

epoxidize styrene and ring open with br2
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Offline agrobert

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #2 on: January 25, 2008, 09:05:11 PM »
epoxidize styrene and ring open with br2

i like your style
In the realm of scientific observation, luck is only granted to those who are prepared. -Louis Pasteur

Offline lutesium

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #3 on: January 27, 2008, 06:26:41 AM »
Me too I like your style :)

But can you give me some examples of epoxidation???

Thank you very very very much!


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Offline sjb

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #4 on: January 27, 2008, 07:06:42 AM »
Me too I like your style :)

But can you give me some examples of epoxidation???

Thank you very very very much!


Lutesium...

Racemic? Perhaps something like a peracid, or hydrogen peroxide.

Stereospecific? I think things like Sharpless epoxidation work OK for these substrates, or things like Shi's dioxirane chemistry...

Offline Kryolith

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #5 on: January 27, 2008, 07:16:14 AM »
Here you can find the epoxidation of styrene with a peracid:

http://www.organic-chemistry.org/namedreactions/prilezhaev-reaction.shtm

the treatment of bromohydrines with NaOH yields epoxides, as well.

Stereospecific? I think things like Sharpless epoxidation work OK for these substrates, or things like Shi's dioxirane chemistry...

Jacobsen epoxidations of (Z)-olefines don't need allyl alcohols or functional groups.

Offline lutesium

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #6 on: January 27, 2008, 07:35:50 AM »
Wouldn't a ring opening wih HBr be better???

Offline Kryolith

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #7 on: January 27, 2008, 07:45:33 AM »
epoxidize styrene and ring open with br2

Ring opening to which product?

Wouldn't a ring opening wih HBr be better???

Probably. But let's await sjh9's answer.

Offline lutesium

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #8 on: January 27, 2008, 06:36:52 PM »
Actually the desired product would be 2-Bromo-1-PhenylPropanol but Ethanol would suffice and I found a synthesis at one of the old sites! It uses N-BromoSuccinimide + H2O to build my block from styrene (propenylbenzene) and how can I attach an urea molecule to it??? By the aid of strong bases??? Please help me!!!


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Offline Kryolith

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #9 on: January 27, 2008, 06:42:49 PM »
So now you know how to synthesize 2-bromo-1-phenyl ethanol.  :)

Now you want to attach urea. To which carbon? Do you want to substitute bromide?

Offline lutesium

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #10 on: January 27, 2008, 07:33:21 PM »
Of course to the carbon where Br is located ;) 2nd carbon that means! Thank you very much for your interest Kyrolith!!!


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Offline sjh9

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #11 on: January 27, 2008, 09:52:08 PM »
epoxidize styrene and ring open with br2

Ring opening to which product?

Wouldn't a ring opening wih HBr be better???

Probably. But let's await sjh9's answer.



It turns out that Styrene oxide is sold by aldrich. 

A quick search on sciencedirect.com for "epoxide halogenation" came up with this abstract:

The regioselective ring opening halogenation of some epoxides using elemental iodine and bromine in the presence of a series of pyridine-containing groups has been studied. The epoxides were subject to cleavage by elemental halogen (I2 and Br2) in the presence of isonicotinic hydrazide (isoniazide) under mild reaction conditions in various solvents. In this study, reagents and conditions have been discovered with which the individual halohydrins can be synthesized in high yield and with more than 95% regioselectivity.


Journal of Molecular Catalysis A: Chemical
Volume 215, Issues 1-2, 14 June 2004, Pages 55-62


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Offline Kryolith

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #12 on: January 28, 2008, 03:47:02 AM »
I've never heard of that before. Thanks you for the information.  :)

Offline lutesium

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #13 on: January 30, 2008, 04:51:51 PM »
Nobody knows how to attach the urea???


Lutesium...

Offline Kryolith

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Re: Synthesis of 2-Bromo-1-PhenylEthanol
« Reply #14 on: January 31, 2008, 04:42:55 AM »
A SN2 reaction in basic solution could work...

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