[de5truction]

can it(this mono-sub reaction) be done by reaction the compound with Cl2 in CCl4, at room temperature? would this reaction be feasible with Cl2/FeCl3?
thanks alot!

[Arsenic]

could this be of any help

[de5truction]

thanks for your help arsenic! but was refering to another compound as reagent..
sorry for the misunderstanding, maybe my nomenclature's abit screwed, but here's wad i was asking
what are the possible reagents for the mono substitution of chlorine atom onto the 4th site? presumably that there is a likihood of the 2nd site to be substituted with chlorine as an isomer..

[Albert]

Pay attention, De5truction.
Arsenic gave you the mechanism of almost the same reaction.

An OH (or an NH2 group) has almost the same proprieties of OR group, if we talk about substituted benzenes. They reacts and, according to what I studied, they behave the same, when it comes to add a particular group.

[HP]

If you dont wont to use direct chlorination of your starting compound you may try indirect synthesis route:
First bromination as same as Arsenic show after this converting Br to NH2 with amonia in autoclave or with NaNH2 at room temp.
Second diazotation of NH2 with HNO2/HCl and last step Sandmayer with Cu2Cl2 to your dezired product.

[GCT]

thanks for your help arsenic! but was refering to another compound as reagent..
sorry for the misunderstanding, maybe my nomenclature's abit screwed, but here's wad i was asking
what are the possible reagents for the mono substitution of chlorine atom onto the 4th site? presumably that there is a likihood of the 2nd site to be substituted with chlorine as an isomer..

my guess is that you'll get almost exclusively the para product, you may need to worry about the acidic hydrogen though depending on which reaction/mechanism you wish to employ

[Arsenic]

It must be stressed that the activation of the aromatic ring(benzene) by OCH3(or OH,NH2,..) and CH3 groups allows the reaction to be done in the absence of a lewis acid ( typical of activated benzenes ).

[movies]

I seem to recall that phenols were particularly difficult to mono-halogenate because they were so activated.  Any on know this for sure?

[GCT]

I seem to recall that phenols were particularly difficult to mono-halogenate because they were so activated.  Any on know this for sure?

yeah, I think you're right on that, from what I recall you'll need to convert the phenol to a less active group for halogenation.  

[de5truction]

precisely, that's what im thinking about, only to be called to 'pay attention'..
cause it was an A level qn for chemistry this year, and it was only a 1 step reaction, which is making me wonder how else to be able to mono sub the methylphenol..
my guess was cl2 in ccl4, is it sound?

[Albert]

yeah, I think you're right on that, from what I recall you'll need to convert the phenol to a less active group for halogenation.  

I don't think you need to do it, but if you insist...

However, even using Cl2 and CHCl3 (at 0°C) with your phenol, you should obtain up to 80% of the product you need.

[HP]

For direct chlorination of phenols to monosubstituated product i think reaction with Cl2/Na2CO3 is good idea but then you will chlorinate sodium phenohy compound  

[movies]

Cl₂ would preferentially chlorinate the benzyllic carbon.

[Albert]

Cl2/Na2CO3

Who mentioned Na2CO3?

[HP]

When waters containing phenols and phenol-related compounds are chlorinated, chlorinated phenols are usually formed as follows:

C6H5OH + HOCl   -->   ClC6H4OH + H2
Monochlorophenols   
Monochlorophenols + HOCl   -->   Cl2C6H3OH + H2
Dichlorophenols   
Dichlorophenols + HOCl   -->   Cl3C6H2OH + H2O
So i think the first reaction is useful for the topic purpose...
Cl/Na2CO3 is mild chlorinating system in chlorinating amine for example and why not with phenols