Methanesulfonyl chloride → (E)-4-(3,4-dichlorophenyl)but-3-enyl methanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of Intermediate 2B (986 mg, 4.54 mmol) in CH2Cl2 (20 mL) was added TEA (1.899 mL, 13.63 mmol). The mixture was cooled to 0° C. and methanesulfonyl chloride (0.531 mL, 6.81 mmol) was added dropwise. The reaction was stirred for 45 min at 0° C. then warmed to rt and diluted with water (20 ml) and CH2Cl2 (20 mL). The layers were separated, and the aqueous layer extracted with CH2Cl2. The combined organic extracts were washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated in vacuo to give Intermediate 2C (1.30 g, 97% yield). Intermediate 2C was carried onto the next reaction without further purification. HPLC/MS (Method D) RT=1.10 min, [M-MeSO3H+H]+ 199.1.

Provenance & Evidence