Bromine → Methyl 2-amino-5-bromo-3-nitrobenzoate

HRID 1910205Notes

Reaction equation

HRID 1910205 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[NH2:13].[Br:15]Br>C(O)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([Br:15])[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[NH2:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 607264Methyl 2-amino-3-nitrobenzoate

Product 1

HCID 17984898Methyl 2-amino-5-bromo-3-nitrobenzoateYield 87.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 2.23 g (10.4 mmol) of 2-amino-3-nitro-benzoic acid methyl ester in 12 mL of acetic acid was added dropwise a solution of 0.53 mL (10.4 mmol) of Br2 in 2.0 mL of acetic acid. The mixture was stirred at r.t. for 30 min and poured into 100 g of ice. The solid was collected by filtration and dried to afford 2.5 g (82%) of 2-Amino-5-bromo-3-nitro-benzoic acid methyl ester. 1H NMR (CDCl3, 400 MHz): δ 8.6 (d, 1H), 8.53 (s, 1H), 3.95 (s, 3H) ppm.

Workup

  1. filtrationThe solid was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-e5535a0d334b413790f44413359cea2b
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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