5-bromo-2-methylbenzamide synthesis
- Product Name:5-bromo-2-methylbenzamide
- CAS Number:854633-21-9
- Molecular formula:C8H8BrNO
- Molecular Weight:214.06
79669-49-1
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Yield:854633-21-9 55%
Reaction Conditions:
with ammonium hydroxide;N-ethyl-N,N-diisopropylamine;HATU in N,N-dimethyl-formamide at 20; for 16 h;
Steps:
19.a
To a mixture of 5-bromo-2-methylbenzoic acid (0.538 g, 2.50 mmol) and HATU(1.289 g, 3.390 mmo/) in DMF (8 mL) was added DIPEA (0.800 mL, 4.59 mmol). The mixture was stirred for 10 minutes before addition of NH OH (0.50 mL) and then left stirring for 16 hours at room temperature. The mixture was poured in to water and cooled at 0 °C for 20 minutes before collecting the resulting precipitate via vacuum filtration to give the title compound (169) (0.292 g, 55%); 1H NMR (400 MHz, CDCI3) δ 7.58 (d, J = 2.1 Hz, 1 H), 7.45 (dd, J = 8.2, 2.1 Hz, 1 H), 7.12 (d, J = 8.2 Hz, 1 H), 5.68 (bs, 2H), 2.44 (s, 3H). LCMS Method C: rt 4.89 min; m/z 214, 216 (M+H]
References:
WO2012/110773,2012,A1 Location in patent:Page/Page column 103
21900-41-4
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