Dimethylformamide → 2-Amino-5-bromo-3-methylbenzoic acid

HRID 2427036Notes

Reaction equation

HRID 2427036 reaction equation
N[C:2]1[CH:10]=[CH:9][C:8](Cl)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C[N:13]([CH3:16])C=O.[Br:17]N1C(=O)CCC1=O>O>[NH2:13][C:16]1[C:8]([CH3:7])=[CH:9][C:10]([Br:17])=[CH:2][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 124762-Amino-5-chlorobenzoic acidHCID 67184N-bromobutanimide

Product 1

HCID 118503832-Amino-5-bromo-3-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 1.5 g of 2-amino-5-chlorobenzoic acid and 100 ml of N,N-dimethylformamide was added 1.8 g of N-bromosuccinimide at room temperature, and the mixture was stirred at room temperature for 10 hours. After 30 ml of water was poured into the reaction mixture, the mixture was extracted with ethyl acetate three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 1.2 g of 2-amino-5-bromo-3-methylbenzoic acid of the formula:

Workup

  1. extractionthe mixture was extracted with ethyl acetate three times
  2. washwashed with an aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-59f6f5ea67fa43aca0abac42bf1ca0cd
Source dataset
uspto-grants-2011_06
Patent number
US07968573B2

Reaction notes

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