(3-Bromophenyl)acetic acid → 2-(3-bromophenyl)acetamide

1-Hydroxybenzotriazole (HOBT, 13.82 g, 102.3 mmol), N-ethyldiisopropyl amine (Hunig's base, 13.22 g, 102.3 mmol) and ammonium carbonate (27.0 g, 279.0 mmol) were added to a solution of (3-bromophenyl)acetic acid (20.0 g, 93.0 mmol) in freshly dried and distilled tetrahydrofuran (80 mL) under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 5 minutes and then cooled to 0° C. and stirred at the same temperature for about 1 hour. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCLHCl, 19.61 g, 102.3 mmol) was added at 0° C. under nitrogen atmosphere. The reaction mixture was stirred at room temperature for about 12 hours. The solvent was evaporated under vacuum and water was added. A white solid was obtained which was filtered, washed with water and dried. Yield: 12.69 g.

1. customin freshly dried
2. distillationdistilled tetrahydrofuran (80 mL) under a nitrogen atmosphere
3. temperaturecooled to 0° C.
4. stirringstirred at the same temperature for about 1 hour
5. stirringThe reaction mixture was stirred at room temperature for about 12 hours
6. customThe solvent was evaporated under vacuum and water
7. additionwas added
8. customA white solid was obtained which
9. filtrationwas filtered
10. washwashed with water
11. customdried

ORD record

ord-6e7e639fb1db440782789e3a93073842

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07674811B2