Benzoyl Peroxide → 4-Benzoyl-3,5-dichlorobenzyl bromide

HRID 280666Notes

Reaction equation

HRID 280666 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([Cl:17])[C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:36]N1C(=O)CCC1=O>C1C=CC=CC=1>[C:4]([C:3]1[C:2]([Cl:1])=[CH:15][C:14]([CH2:16][Br:36])=[CH:13][C:12]=1[Cl:17])(=[O:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 136496852,6-Dichloro-4-methylbenzophenone

Product 1

HCID 136496584-Benzoyl-3,5-dichlorobenzyl bromideYield 58%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A refluxing solution of 2,6-dichloro-4-methylbenzophenone (3.44 g, 13.0 mmol) and dibenzoylperoxide (325 mg, 1.34 mmol) in benzene (130 ml) was treated in portions with N-bromosuccinimide (2.75 g, 15.5 mmol). After 3 hours at reflux, the mixture was cooled and evaporated under vacuum. The residue was triturated with diethyl ether (150 ml), filtered, and evaporated under vacuum. The residue was chromatographed on a column of silica gel (250 g) eluted with 4:1 (v/v) hexane-dichloromethane to provide 2.58 g (58%) 4-benzoyl-3,5-dichlorobenzyl bromide, m.p. 111°-113° C.

Workup

  1. temperatureAfter 3 hours at reflux
  2. temperaturethe mixture was cooled
  3. customevaporated under vacuum
  4. customThe residue was triturated with diethyl ether (150 ml)
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe residue was chromatographed on a column of silica gel (250 g)
  8. washeluted with 4:1 (v/v) hexane-dichloromethane

Sources & evidence

ORD record
ord-846f8da558734dd790c965a140f1c408
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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