N-bromobutanimide → Methyl 2-bromo-2-(4-chlorophenyl)acetate

HRID 231828Notes

Reaction equation

HRID 231828 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([Br:13])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 104196Methyl 4-chlorophenylacetate

Product 1

HCID 10777987Methyl 2-bromo-2-(4-chlorophenyl)acetateYield 103.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 102 g (0.55 mole) of methyl (4-chlorophenyl)acetate in 100 ml of carbon tetrachloride was added 97.9 g (0.55 mole) of N-bromosuccinimide. The resulting mixture was refluxed and irradiated with a 500 W bromo lamp for 5 hours. It was then cooled, filtered, and the filtrate was evaporated to dryness to give 150 g (103% yield) of methyl (4-chlorophenyl)bromoacetate.

Workup

  1. temperatureThe resulting mixture was refluxed
  2. customirradiated with a 500 W bromo lamp for 5 hours
  3. temperatureIt was then cooled
  4. filtrationfiltered
  5. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-3293487a67ca4be8bcc533901b7811be
Source dataset
uspto-grants-1989_07
Patent number
US04849434

Reaction notes

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