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

HRID 1493235Notes

Reaction equation

HRID 1493235 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[CH:4]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)[Br:13]

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

Methyl-(4-chlorophenyl)-acetate (102 g, 0.55 mol) was dissolved in carbon tetrachloride (100 ml) and thereto was added N-bromosuccinimide (97.9 g, 0.55 mol). The mixture was refluxed and irradiated with 500W bromo lamp for 5 hours. Then, the mixture was cooled and filtered and the filtrate was concentrated to dryness to obtained methyl-(4-chlorophenyl)bromoacetate (150 g, yield 103%).

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureThen, the mixture was cooled
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-636191cb477f41d7a38a58ebb5aca262
Source dataset
uspto-grants-1991_06
Patent number
US05021435

Reaction notes

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