Phenyltrimethylammonium bromide dibromide → 2-Bromo-2-(4-chlorophenyl)1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone

HRID 635363Notes

Reaction equation

HRID 635363 reaction equation
[Br-:1].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][C:42]([C:44]2([C:48]3[CH:53]=[CH:52][C:51]([Cl:54])=[C:50]([Cl:55])[CH:49]=3)[CH2:47][CH2:46][CH2:45]2)=[O:43])=[CH:37][CH:36]=1>O1CCCC1>[Br:1][CH:41]([C:38]1[CH:37]=[CH:36][C:35]([Cl:34])=[CH:40][CH:39]=1)[C:42]([C:44]1([C:48]2[CH:53]=[CH:52][C:51]([Cl:54])=[C:50]([Cl:55])[CH:49]=2)[CH2:47][CH2:46][CH2:45]1)=[O:43]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 212584342-(4-Chlorophenyl)-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone

Product 1

HCID 212583922-Bromo-2-(4-chlorophenyl)1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanoneYield 109.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyltrimethylammonium tribromide (6.59 g) was added in portions at −5° C. to a stirred solution of 2-(4-chlorophenyl)-1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone (6.2 g) in tetrahydrofuran (150 ml). The mixture was stirred at ambient temperature for 4 hours, allowed to stand at ambient temperature for a further 48 hours, then it was filtered, and the solvent removed in vacuo. The residue was purified via flash chromatography over silica using a 3:97 mixture of ethyl acetate and petroleum ether (b.p. 60-80° C.) as eluant. Appropriate fractions were combined, and the solvents removed in vacuo. The residue was triturated with petroleum ether (b.p. 60-80° C.) (30 ml) and the resulting solid was collected by filtration and dried in vacuo at ambient temperature to give 2-bromo-2-(4-chlorophenyl)1-[1-(3,4-dichlorophenyl)cyclobutyl]ethanone as a colourless solid (4.83 g), m.p. 109-110° C.

Workup

  1. waitto stand at ambient temperature for a further 48 hours
  2. filtrationit was filtered
  3. customthe solvent removed in vacuo
  4. customThe residue was purified via flash chromatography over silica using
  5. additiona 3:97 mixture of ethyl acetate and petroleum ether (b.p. 60-80° C.) as eluant
  6. customthe solvents removed in vacuo
  7. customThe residue was triturated with petroleum ether (b.p. 60-80° C.) (30 ml)
  8. filtrationthe resulting solid was collected by filtration
  9. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-8806deedaff84b24b4cd6cfe5560c230
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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