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

HRID 1687780Notes

Reaction equation

HRID 1687780 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-b16136b201154ca4b8b9da346d7ce0a6
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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