4-Methylbenzophenone → 4-(Bromomethyl)benzophenone

HRID 931690Notes

Reaction equation

HRID 931690 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[Br:16]Br>C1C=CC=CC=1>[Br:16][CH2:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 86524-MethylbenzophenoneHCID 24408Bromine

Product 1

HCID 1229514-(Bromomethyl)benzophenoneYield 103.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

4-methylbenzophenone (10.0 g; 51.0 mmol) was dissolved in benzene (60 mL) and the solution was warmed to reflux. Solution of bromine (8.39 g; 52.5 mmol) in benzene (15 mL) was added to the reaction mixture over 10 h. The reaction was refluxed for a further 6 h until a light orange solution in obtained and all bromine is consumed. The benzene solvent was evaporated and crude product was obtained as an off-white solid. Recrystallisation from methanol (130 mL) provided 4-(bromomethyl)benzophenone (14.5 g; 69% yield) as a white crystalline solid.

Workup

  1. temperaturethe solution was warmed to reflux
  2. temperatureThe reaction was refluxed for a further 6 h until a light orange solution
  3. customin obtained
  4. customall bromine is consumed
  5. customThe benzene solvent was evaporated
  6. customcrude product was obtained as an off-white solid
  7. customRecrystallisation from methanol (130 mL)

Sources & evidence

ORD record
ord-ba480960cb3345dd8faafc3c56f111b0
Source dataset
uspto-grants-2016_03
Patent number
US09296835B2

Reaction notes

Loading…