Phenyltrimethylammonium bromide dibromide → 2-Bromo-1-(4-chlorobenzo[b]thiophen-2-yl)butan-1-one

HRID 2183644Notes

Reaction equation

HRID 2183644 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11](=[O:15])[CH2:12][CH2:13][CH3:14])[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br-:16].[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>O1CCCC1>[Br:16][CH:12]([CH2:13][CH3:14])[C:11]([C:8]1[S:7][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[C:10]=2[CH:9]=1)=[O:15]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 224736901-(4-Chlorobenzo[b]thiophen-2-yl)butan-1-one

Product 1

HCID 224739972-Bromo-1-(4-chlorobenzo[b]thiophen-2-yl)butan-1-oneYield 148.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-chlorobenzo[b]thiophen-2-yl)butan-1-one (0.93 g), phenyltrimethylammonium tribromide (1.47 g) and tetrahydrofuran (20 ml) was stirred under nitrogen at ambient temperature for 66 hours, then it was filtered and diluted with water (50 ml). The product was extracted into dichloromethane (3×30 ml), the combined extracts were dried (MgSO4) and the solvents were removed in vacuo. The residue was purified by flash chromatography over silica using dichloromethane as eluant. Appropriate fractions were combined and the solvents removed in vacuo to leave 2-bromo-1-(4-chlorobenzo[b]thiophen-2-yl)butan-1-one (1.07 g) which was used without further purification.

Workup

  1. filtrationit was filtered
  2. additiondiluted with water (50 ml)
  3. extractionThe product was extracted into dichloromethane (3×30 ml)
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. customthe solvents were removed in vacuo
  6. customThe residue was purified by flash chromatography over silica
  7. customthe solvents removed in vacuo

Sources & evidence

ORD record
ord-a456adcc477d42818d7603c3c6875f78
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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