N-bromobutanimide → Methyl alpha-bromo-2-chlorophenylacetate

HRID 1903266Notes

Reaction equation

HRID 1903266 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[Br:13]N1C(=O)CCC1=O>Br.C(Cl)(Cl)(Cl)Cl>[Br:13][CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 93683Methyl (2-chlorophenyl)acetate

Product 1

HCID 10730282Methyl alpha-bromo-2-chlorophenylacetate

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A stirred mixture of 36.9 g. of methyl o-chlorophenylacetate, 36.0 g. of N-bromosuccinimide, and 2 drops of 48% hydrobromic acid in 500 ml. of carbon tetrachloride is refluxed for 20 hours and then filtered through magnesium silicate. Evaporation under reduced pressure gives methyl α-bromo-o-chlorophenylacetate as a straw-colored liquid.

Workup

  1. additionA stirred mixture of 36.9 g
  2. filtrationfiltered through magnesium silicate
  3. customEvaporation under reduced pressure

Sources & evidence

ORD record
ord-5d25e86f9cc14ce1bdc85697fd033999
Source dataset
uspto-grants-1984_03
Patent number
US04435419

Reaction notes

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