Dimethylformamide → 5-Bromomethyl-2chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

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Reaction Steps

To a stirred solution of 5-bromomethyl-2-chloro-benzoic acid (Example 71a, 12.4 g) in dichloromethane (250 ml) and dimethylformamide (0.12 ml) at 0° C. was added oxalyl chloride (8.7 ml). The cooling bath was removed and the solution allowed to warm to room temperature. Once gas evolution had ceased the solution was concentrated in vacuo. The residue was redissolved in dichloromethane (300 ml), cooled to 0° C. and treated with diisopropylethylamine (12.4 ml) and adamantylmethylamine (7.54 ml). After 15 min, at 0° C. the solution was poured into diethyl ether (1 L) and washed with 1 N aqueous hydrochloric acid followed by brine. The organics were dried over magnesium sulphate and concentrated in vacuo to give the title compound as a white powder (19 g)

Provenance & Evidence