N-bromobutanimide → HCID 13649655, compound

HRID 280643Notes

Reaction equation

HRID 280643 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH3:15])[CH:11]=[CH:12][C:13]=2[Cl:14])=[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:3]=[CH:4][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=2[Cl:14])[CH2:15][Br:18])=[O:7])=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13649650HCID 13649650, compound

Product 1

HCID 13649655HCID 13649655, compoundYield 50.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Procedure

A refluxing solution of 3-(4-chlorobenzoyl)-4-chlorotoluene (5.3 g, 20. mmol) and dibenzoylperoxide (200 mg, 0.83 mmol) in benzene (200 ml) was treated in portions with N-bromosuccinimide (4.4 g, 25. mmol) over 20 minutes. The mixture was refluxed 15 hours, cooled and filtered. The filtrate was evaporated under vacuum, triturated with diethyl ether (150 ml), filtered, and evaporated under vacuum. The residue was chromatographed on silica gel (500 g) eluted with 97:3 (v/v) n-hexane-ethyl acetate using a preparative high-performance liquid chromatograph to provide 3.47 g (50%) of 3-(4-chlorobenzoyl)-4-chlorobenzyl bromide, m.p. 81°-83° C.

Workup

  1. temperatureThe mixture was refluxed 15 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated under vacuum
  5. customtriturated with diethyl ether (150 ml)
  6. filtrationfiltered
  7. customevaporated 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 high-performance liquid chromatograph

Sources & evidence

ORD record
ord-9f1e900c8a4a4ef4a9898a9c374a3f02
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

Loading…