1-(4-Chlorobenzo[b]thien-2-yl)ethanone → HCID 22473621, compound

HRID 2183589Notes

Reaction equation

HRID 2183589 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11](=[O:13])[CH3:12])[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br-:14].[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:14][CH2:12][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:13]

Participants

4

Reactant 2

HCID 123986281-(4-Chlorobenzo[b]thien-2-yl)ethanoneHCID 17977687Phenyltrimethylammonium bromide dibromide

Product 1

HCID 22473621HCID 22473621, compoundYield 124%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-chlorobenzo[b]thiophen-2-yl]ethan-1-one (1.67 g), phenyltrimethylammonium tribromide (2.98 g) and tetrahydrofuran (40 ml) was stirred under nitrogen at ambient temperature for 22.5 hours then it was filtered and diluted with water (150 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]ethan-1-one (1.65 g) as an off-white solid, m.p. 116-118° C.

Workup

  1. filtrationit was filtered
  2. additiondiluted with water (150 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-3fcd3f1f0c7443b7baba08706dd00a10
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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