N-bromobutanimide → 5-Amino-2-bromo-4-methylbenzoic acid

HRID 1716952Notes

Reaction equation

HRID 1716952 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[Br:12]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[C:4]([CH:3]=1)[C:5]([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 755683-Amino-4-methylbenzoic acid

Product 1

HCID 533302755-Amino-2-bromo-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution (5° C.) of 3-amino-4-methylbenzoic acid (412.2 g, 2.72 mole) in DMF (2.2 L) was added N-bromosuccinimide (495.1 g, 2.78 mole) in small portions at such a rate that the reaction mixture temperature was kept below 15° C. After being stirred for one hour, the reaction mixture was poured onto ice water (1.2 L) with stirring. The solid that formed was filtered, and the filter cake was washed with ice water (3×2 L) and then dried at 60° C. to give a pink solid. Yield: 546 g (87%). 1H NMR (DMSO-d6, 300 MHz): δ 7.20 (s, 1H), 7.04 (s, 1H), 2.05 (s, 3H).

Workup

  1. customwas kept below 15° C
  2. additionthe reaction mixture was poured onto ice water (1.2 L)
  3. stirringwith stirring
  4. customThe solid that formed
  5. filtrationwas filtered
  6. washthe filter cake was washed with ice water (3×2 L)
  7. customdried at 60° C.
  8. customto give a pink solid

Sources & evidence

ORD record
ord-fbf68f2f58154f849bbbd5869c8c3106
Source dataset
uspto-grants-2010_09
Patent number
US07803778B2

Reaction notes

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