Acetic Acid → 2-Amino-5-bromo-3-fluoro-N-methyl-benzamide

HRID 1041438Notes

Reaction equation

HRID 1041438 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].C(O)(=O)C.[Br:17]Br>>[NH2:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([Br:17])=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 272815042-Amino-3-fluoro-n-methylbenzamide

Product 1

HCID 672637462-Amino-5-bromo-3-fluoro-N-methyl-benzamide

Procedure

2-Amino-3-fluoro-N-methyl-benzamide (10.0 g, 59.5 mmol) was dissolved in acetic acid (100 mL, 176 mmol) and bromine (3.22 mL, 62.4 mmol) was added. The reaction was stirred at room temperature for 20 minutes and the precipitate was then collected by filtration and washed with ethyl ether. The white solid was dried overnight under high vacuum at 50° C. to obtain 2-amino-5-bromo-3-fluoro-N-methyl-benzamide; hydrobromide as a white solid (16.8 g, 86%). LCMS (m/e) 216 (M-NHCH3); 1H-NMR (d6-DMSO, 400 MHz) δ 8.49-8.38 (m, 1H), 7.83-7.46 (m, 3H), 7.54 (s, 1H), 7.43 (d, 1H, J=10.89 Hz), 2.72 (d, 3H, J=4.2 Hz); 19F-NMR (d6-DMSO, 400 MHz) δ 131.

Workup

  1. filtrationthe precipitate was then collected by filtration
  2. washwashed with ethyl ether
  3. customThe white solid was dried overnight under high vacuum at 50° C.

Sources & evidence

ORD record
ord-17876468463145949e96dcec8c5f0a15
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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