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

HRID 362252

Reaction equation

HRID 362252 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].O>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

5

Reactant 3

HCID 962WaterHCID 143163-AcetylbenzothiopheneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 27763411-(1-Benzothiophen-3-yl)-2-bromoethan-1-oneYield 63.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of phenyltrimethylammonium tribromide (9.6 g) in tetrahydrofuran (20 ml) was added dropwise over 15 minutes at ambient temperature to a stirred solution of 3-acetylbenzo[b]thiophen (5 g) in tetrahydrofuran (50 ml), then the mixture was stirred at ambient temperature for 35 minutes. Water (100 ml) was added, and the resulting solid was collected by filtration, washed with water (2×50 ml) and dried in vacuo at ambient temperature to give 3-(2-bromoacetyl)benzo[b]thiophen as a white solid (2.4 g).

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water (2×50 ml)
  3. customdried in vacuo at ambient temperature

Sources & evidence

ORD record
ord-e74de6196c624e248c5ab4cf967bba06
Source dataset
uspto-grants-1999_02
Patent number
US05869492

Linked notes

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