Benzoyl Peroxide → 4-(4-Chlorobenzoyl)-3,5-dichlorobenzyl bromide

HRID 280651Notes

Reaction equation

HRID 280651 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([CH3:15])=[CH:10][C:9]=2[Cl:16])=[O:7])=[CH:4][CH:3]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:37]N1C(=O)CCC1=O>C1C=CC=CC=1>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C:8]2[C:13]([Cl:14])=[CH:12][C:11]([CH2:15][Br:37])=[CH:10][C:9]=2[Cl:16])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 136496514-(4-Chlorobenzoyl) 3,5-dichlorotoluene

Product 1

HCID 136496564-(4-Chlorobenzoyl)-3,5-dichlorobenzyl bromideYield 35.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A refluxing solution of 4-(4-chlorobenzoyl)-3,5-dichlorotoluene (7.19 g, 24.0 mmol) and dibenzoylperoxide (370 mg, 1.53 mmol) in benzene (247 ml) was treated in portions with N-bromosuccinimide (7.53 g, 42.3 mmol). The mixture was refluxed 24 hours, cooled, and filtered. The precipitate was washed once with benzene, and the combined filtrate and washings were evaporated under vacuum. The residue was triturated with diethyl ether and filtered, and the filtrate was evaporated under vacuum. The residue was chromatographed on silica gel (500 g) eluted with 7:3 (v/v) n-hexanedichloromethane using a preparative high-performance liquid chromatograph to provide 3.2 g (35%) of 4-(4-chlorobenzoyl)-3,5-dichlorobenzyl bromide, m.p. 69°-73° C.

Workup

  1. temperatureThe mixture was refluxed 24 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washThe precipitate was washed once with benzene
  5. customthe combined filtrate and washings were evaporated under vacuum
  6. customThe residue was triturated with diethyl ether
  7. filtrationfiltered
  8. customthe filtrate was evaporated under vacuum
  9. customThe residue was chromatographed on silica gel (500 g)
  10. washeluted with 7:3 (v/v) n-hexanedichloromethane

Sources & evidence

ORD record
ord-10ef9516df164f2894176c33c1a86856
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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