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0 °C

3-Bromo-4-methylbenzoic acid (1.5 g, 7.0 mmol) in thionyl chloride (10 mL) was heated to 80° C. for 1 h. The solvent was removed in vacuo and the residue was dissolved in DCM (16 mL) at 0° C. under argon before adding ammonium chloride (410 mg, 7.7 mmol) and Et3N (2.43 mL, 17.4 mmol). The reaction was stirred at 0° C. for 15 min then allowed to warm to rt over 16 h. The solvent was removed in vacuo and the mixture partitioned between EtOAc (120 mL) and 1M NaOH (60 mL). The organic phase was washed with 1M NaOH (60 mL), brine (60 mL) and dried (MgSO4). The solvent was removed in vacuo. Trituration with ether and then MeOH gave the title compound: RT=2.78 min; m/z (ES+)=214.0 [M+H]+.

1. customThe solvent was removed in vacuo
2. dissolutionthe residue was dissolved in DCM (16 mL) at 0° C. under argon
3. temperatureto warm to rt over 16 h
4. customThe solvent was removed in vacuo
5. customthe mixture partitioned between EtOAc (120 mL) and 1M NaOH (60 mL)
6. washThe organic phase was washed with 1M NaOH (60 mL), brine (60 mL)
7. dry with materialdried (MgSO4)
8. customThe solvent was removed in vacuo