Carbon tetrabromide → methyl (1R,3S)-3-(bromomethyl)cyclopentane-1-carboxylate

Participants

Reaction Steps

To a 0° C. solution of 99 (6.6 gm, 50 mmol, 1 equi.) in 60 mL of DCM was added triphenyl phosphine (60 mmol, 1.2 equi, 15.72 gm) followed by carbon tetrabromide (60 mmol, 1.2 equi. 19.86 gm). The reaction mixture was stirred overnight allowing the temperature to rise to room temperature. Reaction was concentrated to dryness and the residue was diluted with ether/DCM (1:1, 20 ml) and filtered through a pad of celite. The filtrate was concentrated to dryness and the residue was purified by silica gel chromatography with (5% to 20% EtOAc in hexanes) to provide 3.5 g of (1R,3S)-methyl 3-(bromomethyl)cyclopentanecarboxylate 100.

Provenance & Evidence