Water → HCID 20498427, compound

Participants

Reaction Conditions

Reaction Steps

The contents of a 10 ml flask charged with 1,1,1-tribromo-3-methyl-2-butanol (1.7 mmol), mesyl chloride (1.9 mmol) and pyridine (6 ml) were stirred at 20° C. for 16 hours. Then, the reaction mixture was poured out into water (50 ml), then extracted with three 15 ml-portions of dichloromethane, the combined extract phases were washed with 15 ml 36% (w) aqueous hydrochloric acid, dried over anhydrous magnesium sulphate and the solvent was evaporated from the dried liquid to leave a residue (0.9 g) of methyl 1,1,1-tribromo-3-methyl-2-butyl sulphonate (compound 13). The contents of a 10-ml flask charged with this sulphonate (0.50 mmol), zinc powder (0.75 mmol), diethyl ether (2.5 ml) and glacial acetic acid (0.5 ml) were stirred at 20° C. for 30 min. The sulphonate was fully converted, with a selectivity to the title compound of 82%.

Provenance & Evidence