N-bromobutanimide → 4-(4-Fluorobenzoyl)benzyl bromide

HRID 1421551Notes

Reaction equation

HRID 1421551 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:16][CH:15]=2)=[O:7])=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 47290124-Fluoro-4'-methylbenzophenone

Product 1

HCID 47290134-(4-Fluorobenzoyl)benzyl bromideYield 91.4%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A carbon tetrachloride solution (200 ml) of 4-fluoro-4'-methylbenzophenone (16 g), N-bromosuccinimide (14.2 g) and 2,2'-azodi-isobutyronitrile (0.1 g) was heated for 16 hours with refluxing. After the mixture was cooled to a room temperature, the precipitates were collected by filtration, and the solvent was distilled off to obtain 4-bromomethyl-4'-fluorobenzophenone (20 g).

Workup

  1. temperaturewith refluxing
  2. filtrationthe precipitates were collected by filtration
  3. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-f6e9fbb7678d4f1d86035e647fe9bc1c
Source dataset
uspto-grants-2000_06
Patent number
US06077866

Reaction notes

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