Methanesulfonyl chloride → HCID 21477178, compound

Participants

Reaction Conditions

Reaction Steps

To a flame-dried flask containing a solution of 1-(3-bromophenyl)propanol of Preparation 38 (3.50 g) and triethylamine (4.54 mL) in dry methylene chloride (18 mL) at 0° C. under nitrogen is added methanesulfonyl chloride (1.39 mL) over 1 min. The resulting mixture is stirred at 0° C. for 2 hrs, diluted with water (8 mL), and the layers are separated. The aqueous phase is extracted with methylene chloride (25 mL) and the combined organic phase is washed with saline (5 mL), dried over sodium sulfate, and concentrated under reduced pressure to give an oily intermediate. A mixture containing the intermediate and lithium bromide (1.42g) in acetone (50 mL) under nitrogen is refluxed for 4 hrs, cooled to RT, concentrated to remove acetone, re-diluted with methylene chloride (40 mL) and water (20 mL), and the layers are separated. The aqueous phase is extracted with methylene chloride (40 mL) and the combined organic phase is washed with saline (15 mL), dried over sodium sulfate, and concentrated to give a crude oil which is then chromatographed on silica gel (70-230 mesh, 250 g), eluting with ethyl acetate/hexane (5/95). Pooling of fractions with an Rf =0.63 by TLC (ethyl acetate/hexane, 25/75) and removal of solvent under reduced pressure gives the title compound.

Provenance & Evidence