[OrganicDan96]

I have a Williamson-type ether synthesis reaction I have to do. the literature converted an alcohol to a tosylate ester then reacted this with a phenol salt to give the product. the problem is it takes 6 days to make the tosylate then 14 days (this is partly due to a conformational thing with the phenol) to make the ether product with a poor yield. so my idea was to instead make the triflate ester. as I understand it triflates are extremely reactive towards nucleophiles and I must exclude water as much as possible so work up would be basically impossible and I would not be able to get an NMR of the product easily. so i was thinking if the triflate is made and in the same pot the phenol is added directly, with no need to make the salt due to the reactivity of the triflate leaving group. does this sound like a good idea, could this work?

[Babcock_Hall]

I don't know the answer to your question, but perhaps one of our synthetic specialists will comment.  If tosylate is too cold, and trifluoromethanesulfonate is too hot, tresylate may be just right.  If you try pentafluorobenzenesulfonate, watch out for the possibility of a nucleophilic aromatic substitution that displaces a fluorine atom as fluoride.

[wildfyr]

Would you care to share more about your substrate? Triflate is indeed better, but I doubt its going to cut your reaction down to overnight if it indeed takes weeks. Is it a polymer endgroup? PEG I suspect? I've done the tosylation of PEG and it indeed sucks.

If you are trying to add triflate to a an alcohol, I suggest using triflic anhydride.

And I am not so sure that your triflated alcohol couldn't handle neutral water. There are about a billion citations in the literature. Have a browse and tell us what you find. This was the first result when I Googled "triflic anhydride reaction" http://reag.paperplane.io/00002824.htm

[rolnor]

I have done some triflates, if you make the triflate in diethyl ether and use ethyl diisopropylamine as base, the ethyl diisopropylamine salt will fall out and the solution can be decanted. I usually do the triflate at -78C.  Secondary triflates can be chromatographed on silica and are less reactive.
I think you still need to use base in the reaction with the phenol.

[rolnor]

I once tried to alkylate diethyl malonate with a primary triflate and got pure, O-alkylated product in high yield, this was because triflates are very hard electrophiles.