Ammonia → HCID 86723265, compound

Participants

Reaction Steps

To 2-bromo-5-(ethylsulfonyl)benzoic acid (Preparation 73, 8.10 g, 27.6 mmol) dissolved in THF (200 mL) was added carbonyldiimidazole (8.72 g, 41.4 mmol). The reaction was left to stir for 5 minutes under nitrogen before ammonia was bubbled through the solution. A temperature rise from 22° C. to 41° C. was observed over 10 minutes. The temperature then started to fall, reaching 35° C. after 5 minutes, after which the flow of ammonia was stopped. The reaction mixture was left to stand as a saturated ammonia solution for 30 minutes before removal of the solvent under reduced pressure. The residue was partitioned between EtOAc (500 mL) and water (500 mL) and the layers separated. The organic layer was dried over MgSO4 and the solvent removed under reduced pressure to give the crude product. Trituration with CH2Cl2 gave the title compound as a solid in 28% yield, 2.23 g. A further portion of the title compound was isolated by drying of the filtrate and further trituration, to give a further 8%, 650 mg.

Provenance & Evidence