Chloroacetyl chloride → HCID 86618191, compound

Participants

Reaction Steps

A mixture of 14 g (80 mmol) methyl indole-6-carboxylate, 40 mL (84 mmol) ethylmagnesium chloride (2M) in diethyl ether, 240 mL (240 mmol) zinc chloride (1M) in diethyl ether, 9.5 g (84 mmol) chloroacetyl chloride in 680 mL DCM was stirred at room temperature for 19 h. THF was added and diethyl ether and DCM were removed by evaporation. The mixture was treated with NH4Cl aq. and ethyl acetate. The aqueous phase was extracted with THF/ethyl acetate and the combined organic layers were washed with NaCl aq., dried with Na2SO4 and evaporated. The residue was washed with ethyl acetate and dried under vacuum at 50° C. to yield 4 g (20%) of the title compound as light yellow solid. MS (m/e): 250.1 (M−H).

Provenance & Evidence