Marzi, ElenaMongin, FlorenceSpitaleri, AndreaSchlosser, Manfred2006-03-032006-03-032006-03-03200110.1002/1099-0690(200108)2001:15%3C2911::AID-EJOC2911%3E3.0.CO;2-Whttps://infoscience.epfl.ch/handle/20.500.14299/226984O-Methoxymethyl (MOM) protected fluorophenols can be cleanly metalated and subsequently be submitted to site-selective electrophilic substitution. The 2- and 4-isomers exhibit ambivalent reactivity: deprotonation occurs at the position adjacent to the O when butyllithium is employed whereas the position adjacent to the F is attacked by the superbasic mixt. of butyllithium and K tert-butoxide (LIC-KOR). The MOM-protected (trifluoromethyl)phenols react exclusively at O-neighboring positions. The meta isomer provides another example of optional site selectivity, undergoing H/metal exchange at the 2-position with the LIC-KOR reagent and at the 6-position with sec-butyllithium. Unprotected (trifluoromethyl)phenols can also be ortho-metalated after O-deprotonation, although the products are formed in only moderate yields. [on SciFinder (R)]Phenols Role: RCT (Reactant)RACT (Reactant or reagent) ((trifluoromethyl)phenols; reactant as protected in prepn. of trifluoromethylhydroxybenzoic acid); Phenols Role: RCT (Reactant)RACT (Reactant or reagent) (fluorophenols; reactant as protected influorophenol protected metalation fluorohydroxybenzoic acid prepn; fluoromethylphenol protected metalation fluoromethylhydroxybenzoic acid prepntext::journal::journal article::research article