Oxalyl chloride → HCID 14807709, compound

Participants

Reaction Steps

To a suspension of 5-bromo-1-naphtoic acid (Example 9.1) (10.8 g) in dichloromethane (93 ml) containing 3 drops of dimethylformamide was added oxalyl chloride (4 ml) and the reaction mixture stirred at ambient temperature for 6 hours. The solution was concentrated to afford a white solid which was re-dissolved in tetrahydrofuran. The solution was cooled to 2° C. and a solution of potassium tert-butoxide (7.2 g) in tetrahydrofuran (148 ml) was added dropwise and the reaction mixture stirred at ambient temperature for 3 hours. The solution was poured onto ice and extracted with ethyl acetate. The combined organic extracts were washed with water, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate) to give 5-bromo-1-naphtoic acid tert-butyl ester (12 g). 1H-NMR (CDCl3, 400 MHz): 8.82 (d, 1H), 8.46 (d, 1H), 8.11 (d, 1H), 7.72 (d, 1H), 7.60 (m, 1H), 7.40 (m, 1H), 1.70 (s, 9H).

Provenance & Evidence