4-Methylbenzophenone → 4-(Bromomethyl)benzophenone

HRID 40448

Reaction equation

HRID 40448 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]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[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 67184N-bromobutanimide

Product 1

HCID 1229514-(Bromomethyl)benzophenoneYield 72.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred mixture of 4-methyl benzophenone (1) (15.0 g, 76 mmol) and N-bromo succinimide (14.2 g, 80 mmoll) in chloroform (100 ml) was heated to reflux for 18 h. with a 100W bulb shining 2 cm from the flask. The reaction mixture was cooled, washed with water and concentrated in vacuo. The resulting solid was washed with diethyl ether to leave 2 (15.1 g, 72%) as a white solid; δH (CDCl3) 4.55 (2H, s, CH2Br), 7.46-7.84 (9H, m, Ar—H).

Workup

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water
  4. concentrationconcentrated in vacuo
  5. washThe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-8ef8eb7b19054ea99663eae47e63f478
Source dataset
uspto-grants-2013_09
Patent number
US08530212B2

Linked notes

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