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

HRID 1988389Notes

Reaction equation

HRID 1988389 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-8924183b1f654745bf1ae6750523d990
Source dataset
uspto-grants-2009_06
Patent number
US07553972B2

Reaction notes

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