Phenyltrimethylammonium bromide dibromide → HCID 21258424, compound

HRID 635360Notes

Reaction equation

HRID 635360 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:36]=[C:37]([C:42]2([C:46](=[O:54])[CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH2:45][CH2:44][CH2:43]2)[CH:38]=[CH:39][C:40]=1[Cl:41]>O1CCCC1>[Br:1][CH:47]([C:48]1[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=1)[C:46]([C:42]1([C:37]2[CH:38]=[CH:39][C:40]([Cl:41])=[C:35]([Cl:34])[CH:36]=2)[CH2:45][CH2:44][CH2:43]1)=[O:54]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 21258420HCID 21258420, compound

Product 1

HCID 21258424HCID 21258424, compoundYield 153.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyltrimethylammonium tribromide (4.02 g) was added in portions at −10° C. to a stirred solution of 1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-phenylethanone (3.41 g) in tetrahydrofuran (100 ml). The mixture was stirred at ambient temperature for 4 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 to give 2-bromo-1-[1-(3,4-dichlorophenyl)cyclobutyl]-2-phenylethanone as a colourless oil (3.8 g).

Workup

  1. filtrationit was filtered
  2. customthe solvent removed in vacuo
  3. customThe residue was purified via flash chromatography over silica using
  4. additiona 3:97 mixture of ethyl acetate and petroleum ether (b.p. 60-80° C.) as eluant
  5. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-b73243790aaa4904bc96880985b53f0f
Source dataset
uspto-grants-2001_02
Patent number
US06187802B1

Reaction notes

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