4-Methylbenzophenone → 4-(Bromomethyl)benzophenone

HRID 1797274Notes

Reaction equation

HRID 1797274 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)benzophenone

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A stirred mixture of 4-methylbenzophenone (15.02 g, 76.6 mmol) and N-bromosuccinimide (14.2 g, 79.8 mmol) in CHCl3 (100 cm3) was heated under gentle reflux for 18 h with a 100 W bulb shining 2 cm from the flask. The reaction mixture was washed with water, dried (MgSO4) and solvent was removed in vacuo). The resulting solid was then washed with Et2O to remove any starting material to leave the product as a white solid (15.07 g, 71.5%, mp 110–112° C. (lit. 110–111°); δH (200 MHz; CDCl3) 4.55 (2 H, s, CH2Br), 7.46–7.70 (5 H, m, ArH), 7.80–7.9 (4 H, m, ArH o- to C═O); m/z 277 ([M81Br+H]+, 25%) and 275 ([M79Br+H]−, 25%), 197 (100%).

Workup

  1. temperaturewas heated
  2. temperatureunder gentle reflux for 18 h with a 100 W bulb
  3. washThe reaction mixture was washed with water
  4. dry with materialdried (MgSO4) and solvent
  5. customwas removed in vacuo)
  6. washThe resulting solid was then washed with Et2O
  7. customto remove any starting material

Sources & evidence

ORD record
ord-300956b7c6bb4da39126fb78cea48ace
Source dataset
uspto-grants-2006_04
Patent number
US07034129B2

Reaction notes

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