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ChemicalBook CAS DataBase List 4-Ethoxy-2,6-difluorobenzamide

4-Ethoxy-2,6-difluorobenzamide synthesis

4synthesis methods
-

Yield:916483-57-3 93%

Reaction Conditions:

Stage #1: 4-ethoxy-2,6-difluorobenzoic acidwith oxalyl dichloride;N,N-dimethyl-formamide in dichloromethane at 18 - 25;
Stage #2: with ammonia in tetrahydrofuran;water;

Steps:

1.c

c) Oxalyl chloride (3.17 ml, 36.4 mmol) was added dropwise to a stirred suspension of 4-ethoxy-2,6-difluorobenzoic acid (3.5 g, 17.3 mmol) and dimethylformamide (5 drops) in dichloromethane (50 ml). The resulting solution was stirred at room temperature for 4 hours and was then evaporated. The residue was dissolved in tetrahydrofuran and then added dropwise to a vigorously stirring 35% aqueous ammonia solution (60 ml). The mixture was filtered and the residue was washed with ice-cold water and then dried under vacuum to leave 4-ethoxy-2,6-difluorobenzamide as a colourless solid (3.23 g, 93% yield):1H-NMR (DMSO d6): 7.91 (br. s, 1H), 7.65 (br. s, 1H), 6.78-6.71 (m, 2H), 4.08 (q, 2H), 1.32 (t, 3H).MS (+ve EI): 201 (M+)

References:

US2010/168143,2010,A1 Location in patent:Page/Page column 12