3-Acetylbenzothiophene → 1-(1-Benzothiophen-3-yl)-2-bromoethan-1-one

HRID 362254Notes

Reaction equation

HRID 362254 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.[C:34]([C:37]1[C:38]2[CH:45]=[CH:44][CH:43]=[CH:42][C:39]=2[S:40][CH:41]=1)(=[O:36])[CH3:35]>O1CCCC1>[Br:1][CH2:35][C:34]([C:37]1[C:38]2[CH:45]=[CH:44][CH:43]=[CH:42][C:39]=2[S:40][CH:41]=1)=[O:36]

Participants

4

Reactant 2

HCID 143163-AcetylbenzothiopheneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 27763411-(1-Benzothiophen-3-yl)-2-bromoethan-1-oneYield 105.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phenyltrimethylammonium tribromide (26.32 g) was added in portions over 45 minutes at -5° C. under nitrogen to a stirred solution of 3-acetylbenzo[b]thiophen (12.34 g) in tetrahydrofuran (100 ml), then the mixture was stirred at ambient temperature for 1 hour. The resulting solid was collected by filtration, washed with ether (100 ml), dried in vacuo at ambient temperature, and crystallised from ethanol to give 3-(2-bromoacetyl)benzo[b]thiophen as a white solid (10.9 g).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. washwashed with ether (100 ml)
  3. customdried in vacuo at ambient temperature
  4. customcrystallised from ethanol

Sources & evidence

ORD record
ord-0e71f0129730448488e796e0805809e6
Source dataset
uspto-grants-1999_02
Patent number
US05869492

Reaction notes

Loading…