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A large-scale synthesis of  meso -2,3-difluoro-1,4-butanediol in 5 steps from ( Z )-but-2-enediol is described. Crystallographic analysis of the diol and the corresponding benzyl ether reveals an  anti  conformation of the vicinal difluoride moiety. Monosilylation of the diol is high-yielding but all attempts to achieve chain extension through addition of alkyl Grignard and acetylide nucleophiles failed.

Synthesis and crystallographic analysis of meso-2,3-difluoro-1,4-butanediol and meso-1,4-dibenzyloxy-2,3-difluorobutane