Hydrochloric Acid → HCID 23154554, compound

HRID 556772Notes

Reaction equation

HRID 556772 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[C:11]1([CH2:17][C:18](Cl)=[O:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([C:18](=[O:19])[CH2:17][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:6]=2[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7679Phenylacetyl chlorideHCID 27765785-Bromo-1-benzothiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23154554HCID 23154554, compoundYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromobenzothiophene (1 g) and phenylacetyl chloride (1.1 g) in dichloromethane (50 mL) was added aluminum chloride (1.9 g) at 0° C. and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was poured into an ice-cooled hydrochloric acid aqueous solution (2 mol/L) and the mixture was extracted with diethyl ether. The organic layer washed with water and brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=8/1). After the solvent was removed, the residual solid washed with hexane to give the title compound (1.1 g).

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=8/1)
  6. customAfter the solvent was removed
  7. washthe residual solid washed with hexane

Sources & evidence

ORD record
ord-0263c834b479498bb621331d8bbb3461
Source dataset
uspto-grants-2011_11
Patent number
US08058245B2

Reaction notes

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