Hydrogen Bromide → Methyl 2-bromo-2-(3-chlorophenyl)acetate

HRID 550837Notes

Reaction equation

HRID 550837 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1.[Br:13]N1C(=O)CCC1=O.Br>Br.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[CH:4]([Br:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 67184N-bromobutanimide2×HCID 2733544Methyl 2-(3-chlorophenyl)acetate

Product 1

HCID 19385736Methyl 2-bromo-2-(3-chlorophenyl)acetateYield 69%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of (3-Chloro-phenyl)-acetic acid methyl ester (2.0 g, 10.8 mmol), N-bromosuccinimide (1.95 g, 11.0 mmol) and 3 drops of hydrobromic acid (48% solution) in chloroform (100 mL) was heated under reflux for three days. Additional amounts of N-bromosuccinimide and hydrobromic acid were added to drive the reaction to completion. The reaction mixture was concentrated to dryness, taken up in methylene chloride and loaded onto a column of silica gel. Elution with 10% ethyl acetate/hexanes gave Bromo-(3-chloro-phenyl)-acetic acid methyl ester (1.95 g, 69% yield) as a colorless oil. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for three days
  3. customthe reaction to completion
  4. concentrationThe reaction mixture was concentrated to dryness
  5. washElution with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a8d5b824d5634c449c06c97195426aa0
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Reaction notes

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