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

HRID 1175290Notes

Reaction equation

HRID 1175290 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-d2b19420a2ac4b21b37c28eb90cf1815
Source dataset
uspto-grants-2010_11
Patent number
US07838498B2

Reaction notes

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