Bromine → 5-(2-Bromo-acetyl)-2-chloro-benzoic acid methyl ester

HRID 456891Notes

Reaction equation

HRID 456891 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[Cl:13].[Br:15]Br>C(O)(=O)C.Br.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([C:10](=[O:12])[CH2:11][Br:15])[CH:7]=[CH:6][C:5]=1[Cl:13]

Participants

5

Reactant 2

HCID 24408BromineHCID 58818179Methyl 5-acetyl-2-chlorobenzoate

Product 1

HCID 588181855-(2-Bromo-acetyl)-2-chloro-benzoic acid methyl esterYield 102.2%

Reagents, catalysts & solvents 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 5-acetyl-2-chloro-benzoic acid methyl ester (100 mg, 0.47 mmol) in glacial acetic acid (5 mL) was added bromine (0.05 mL, 0.94 mmol). The mixture was stirred at room temperature for 2 h. Hydrobromic acid-acetic acid (2 drops, 30%) was added and the mixture was stirred for 10 minutes. The mixture was concentrated in vacuo to afford the title compound (140 mg).

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-7d952decae654fb691265f7365789614
Source dataset
uspto-grants-2007_03
Patent number
US07186742B2

Reaction notes

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