N-bromobutanimide → HCID 13649657, compound

HRID 280669Notes

Reaction equation

HRID 280669 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1)=[O:5].[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:16]=[CH:15][CH:14]=[C:13]([Cl:17])[C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][Br:18])=[CH:10][CH:11]=1)=[O:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13649652(2,6-Dichlorophenyl)(4-methylphenyl)methanone

Product 1

HCID 13649657HCID 13649657, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Procedure

A refluxing mixture of 4-(2,6-dichlorobenzoyl)toluene (12.0 g, 45.2 mmol) and dibenzoylperoxide (90 mg, 0.37 mmol) in benzene (450 ml) was treated in portions with N-bromosuccinimide (8.83 g, 49.6 mmol), refluxed 1.5 hours, cooled, and evaporated to dryness under vacuum. The residue was triturated with diethyl ether (300 ml), filtered, and the filtrate was evaporated to dryness under vacuum. The crude product was chromatographed on a column of silica gel (700 g) eluted with 97:3 (v/v) hexaneethyl acetate to provide 7.49 g (48%) 4-(2,6-dichlorobenzoyl)benzyl bromide, m.p. 126°-130° C.

Workup

  1. temperaturerefluxed 1.5 hours
  2. temperaturecooled
  3. customevaporated to dryness under vacuum
  4. customThe residue was triturated with diethyl ether (300 ml)
  5. filtrationfiltered
  6. customthe filtrate was evaporated to dryness under vacuum
  7. customThe crude product was chromatographed on a column of silica gel (700 g)
  8. washeluted with 97:3 (v/v) hexaneethyl acetate

Sources & evidence

ORD record
ord-5748b3e3c49641c384dfeb7c221b5474
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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