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

HRID 968800Notes

Reaction equation

HRID 968800 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[CH:3]=[C:4]([C:8]([Br:12])=[CH:9][C:10]=1[CH3:11])[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 83.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-amino-4-methylbenzoic acid (13) (5.1525 g, 34.08 mmol)) and DMF (30 mL) is cooled to about 5° C., whereupon N-bromosuccinimide (6.230 g, 35 mmol) is added in small portions, at a rate such that the reaction temperature stays below 10° C. The reaction mixture is then stirred at ambient temperature for about 3 hours and is then added to ice water (150 mL). The solids that form are filtered and dried to provide 3-Amino-6-bromo-4-methylbenzoic Acid (19) (6.5439 g, 83% yield).

Workup

  1. additionis added in small portions, at a rate such that the reaction temperature
  2. customstays below 10° C
  3. filtrationThe solids that form are filtered
  4. customdried

Sources & evidence

ORD record
ord-a8e0fddb530d4d9b8b66c5f87d6aa30f
Source dataset
uspto-grants-2007_12
Patent number
US07304084B2

Reaction notes

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