Phenyltrimethylammonium bromide dibromide → HCID 22474281, compound

HRID 2183617Notes

Reaction equation

HRID 2183617 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11](=[O:14])[CH2:12][CH3:13])[S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br-:15].[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:15][CH:12]([CH3:13])[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:14]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 224738541-(4-Chlorobenzo[b]thien-2-yl)-1-propanone

Product 1

HCID 22474281HCID 22474281, compoundYield 236.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-chlorobenzo[b]thiophen-2-yl)propan-1-one (1.65 g), phenyltrimethylammonium tribromide (2.76 g) and tetrahydrofuran (20 ml) was stirred under nitrogen for 18.5 hours, then it was filtered and diluted with water (200 ml). The product was extracted into dichloromethane (3×40 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)propan-1-one (3.06 g) as a pale yellow solid, m.p. 104-106° C.

Workup

  1. filtrationit was filtered
  2. additiondiluted with water (200 ml)
  3. extractionThe product was extracted into dichloromethane (3×40 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-148214b3cf8749c288f2685d326a55db
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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