Chloroform → 2-Bromo-1,2-di-(4-chlorophenyl)ethanone

HRID 1863351Notes

Reaction equation

HRID 1863351 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1.C(Cl)(Cl)Cl>C(OCC)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:19])[CH:11]([Br:1])[C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 24408BromineHCID 5873181,2-Bis(4-chlorophenyl)ethanone

Product 1

HCID 112216182-Bromo-1,2-di-(4-chlorophenyl)ethanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Bromine (2 ml.) was added dropwise to a solution of p-chloro-2-(p-chlorophenyl)acetophenone (10 g.; 0.038 mole), chloroform (50 ml.) and diethyl ether (25 ml.). The mixture was heated at reflux for 0.5 hours and cooled (ca. 20°). Following a thorough washing with saturated sodium bicarbonate, the organic solution was dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed at low pressure through silica gel 60 mesh (230-400) with 5% ethyl acetate in hexane. Recrystallization from hexane afforded 2.69 g.; m.p. 81.5°-83°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 0.5 hours
  3. temperaturecooled (ca. 20°)
  4. washa thorough washing with saturated sodium bicarbonate
  5. dry with materialthe organic solution was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed at low pressure through silica gel 60 mesh (230-400) with 5% ethyl acetate in hexane
  8. customRecrystallization from hexane
  9. customafforded 2.69 g

Sources & evidence

ORD record
ord-f47039183a414d82a467fb9772ba4efa
Source dataset
uspto-grants-1979_09
Patent number
US04168315

Reaction notes

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