Benzophenone, 4-chloro-4'-methyl- → 4-(4-Chlorobenzoyl)benzyl bromide

HRID 280632Notes

Reaction equation

HRID 280632 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][Br:17])=[CH:10][CH:9]=2)=[O:7])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 21494Benzophenone, 4-chloro-4'-methyl-HCID 67184N-bromobutanimide

Product 1

HCID 98396514-(4-Chlorobenzoyl)benzyl bromideYield 63%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-(4-chlorobenzoyl)toluene (5.48 g, 23.8 mmol), dibenzoylperoxide (100 mg, 0.413 mmol), and N-bromosuccinimide (4.56 g, 25.6 mmol) in carbon tetrachloride (70 ml) was refluxed for 2 hours, cooled, filtered, and evaporated under vacuum. The residue was chromatographed on silica gel (1 kg) eluted with 97:3 (v/v) hexane-ethyl acetate using a preparative high-performance liquid chromatograph. Appropriate fractions were pooled and evaporated under vacuum to provide 4.61 g (63%) of 4-(4-chlorobenzoyl)benzyl bromide, m.p. 103°-104° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customevaporated under vacuum
  5. customThe residue was chromatographed on silica gel (1 kg)
  6. washeluted with 97:3 (v/v) hexane-ethyl acetate using a preparative high-performance liquid chromatograph
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-c7f7b3a2089d4c7a9067e8d23ec14192
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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