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

HRID 1037141Notes

Reaction equation

HRID 1037141 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].C1C(=O)N([Br:19])C(=O)C1>CN(C=O)C>[NH2:1][C:2]1[C:10]([CH3:11])=[CH:9][C:8]([Br:19])=[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 acidYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution (5° C.) of 3-amino-4-methylbenzoic acid (3.02 g, 20 mmol) in DMF (20 mL) was added NBS (3.38 g, 19 mmol) 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 (100 mL) with stirring. The solid formed was collected by filtration, and the filter cake was washed with ice water (3×100 mL) and then dried at 60° C. under high vacuum to give 5-amino-2-bromo-4-methylbenzoic acid (3.55 g, yield 77.5%) as a pink solid. MS: m/z=230.0 (M+1, ESI+).

Workup

  1. customwas kept below 15° C
  2. additionthe reaction mixture was poured onto ice water (100 mL)
  3. stirringwith stirring
  4. customThe solid formed
  5. filtrationwas collected by filtration
  6. washthe filter cake was washed with ice water (3×100 mL)
  7. customdried at 60° C. under high vacuum

Sources & evidence

ORD record
ord-797f07373c71439bb260691f826dd71e
Source dataset
uspto-grants-2013_10
Patent number
US08546357B2

Reaction notes

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