Chlorobenzene → 1-(4-(Bromomethyl)-2-chlorophenyl)ethanone

HRID 516968

Reaction equation

HRID 516968 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].ClC1C=CC=CC=1.[Br:19]N1C(=O)CCC1=O>C1(C)C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:19][CH2:8][C:6]1[CH:5]=[CH:4][C:3]([C:9](=[O:11])[CH3:10])=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 3

HCID 7964ChlorobenzeneHCID 67184N-bromobutanimideHCID 155609491-(2-Chloro-4-methylphenyl)ethanone

Product 1

HCID 898539141-(4-(Bromomethyl)-2-chlorophenyl)ethanoneYield 70%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
142.5 °C

Procedure

A mixture of 1-(2-chloro-4-methylphenyl)ethanone (1.6 g, 9.50 mmol) (preparation 15) and chlorobenzene (60 ml) was prepared at room temperature and N-bromosuccinimide (NBS) (1.86 g, 10.44 mmol) added followed by a catalytic amount of benzoyl peroxide (ca. 1.5 mg, 0.005 mmol), and the resulting mixture was heated to 140-145° C. for 16 h. The mixture was then allowed to cool to room temperature, diluted with toluene (50 ml) and filtered through a celite pad. The pad was washed with toluene (2×50 ml) and the filtrate concentrated under reduced pressure and purified by column chromatography (0-10% EtOAc/Hexanes) to afford 1-(4-(bromomethyl)-2-chlorophenyl)ethanone (1.65 g, 6.65 mmol, 70%) as a yellow oil.

Workup

  1. customwas prepared at room temperature
  2. temperatureto cool to room temperature
  3. filtrationfiltered through a celite pad
  4. washThe pad was washed with toluene (2×50 ml)
  5. concentrationthe filtrate concentrated under reduced pressure
  6. custompurified by column chromatography (0-10% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-63c8c2c23ef14ab3a813d19d099ced27
Source dataset
uspto-grants-2015_08
Patent number
US09115088B2

Linked notes

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