N-bromobutanimide → 4-(4-Chlorobenzoyl)-3-chlorobenzyl bromide

HRID 280639Notes

Reaction equation

HRID 280639 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=2[Cl:15])=[O:7])=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][Br:18])=[CH:10][C:9]=2[Cl:15])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 136496494-(4-Chlorobenzoyl)-3-chlorotoluene

Product 1

HCID 136496544-(4-Chlorobenzoyl)-3-chlorobenzyl bromideYield 49.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalyst2×HCID 241BenzeneSolvent

Procedure

A stirred refluxing solution of 4-(4-chlorobenzoyl)-3-chlorotoluene (2.65 g, 9.99 mmol) and dibenzoylperoxide (100 mg, 0.413 mmol) in benzene (100 ml) was treated in portions with an intimate mixture of N-bromosuccinimide (2.2 g, 12. mmol) and dibenzoylperoxide (100 mg, 0.413 mmol). The mixture was refluxed 1.5 hours, cooled, and filtered. The filtrate was evaporated under vacuum, triturated with diethyl ether (100 ml), and filtered. The filtrate was evaporated under vacuum and the residue was chromatographed on silica gel (500 g) eluted with 97:3 (v/v) n-hexane-ethyl acetate using a preparative highperformance liquid chromatograph to provide 1.69 g (49%) of 4-(4-chlorobenzoyl)-3-chlorobenzyl bromide, m.p. 88°-90° C.

Workup

  1. temperatureThe mixture was refluxed 1.5 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated under vacuum
  5. customtriturated with diethyl ether (100 ml)
  6. filtrationfiltered
  7. customThe filtrate was evaporated under vacuum
  8. customthe residue was chromatographed on silica gel (500 g)
  9. washeluted with 97:3 (v/v) n-hexane-ethyl acetate using a preparative highperformance liquid chromatograph

Sources & evidence

ORD record
ord-f82d02ae12bd4e0cbd96e9329d9ca9e1
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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