Hydrochloric Acid → HCID 70073828, compound

HRID 344264Notes

Reaction equation

HRID 344264 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[S:10]1[CH:14]=[CH:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]1=2.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([C:14]1[S:10][C:11]2[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=2[CH:13]=1)=[O:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7221Benzo(B)ThiopheneHCID 898486-Bromohexanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 70073828HCID 70073828, compoundYield 15.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-Bromohexanoyl chloride (2 g) and benzo[b]thiophene (1.26 g) were dissolved in methylene chloride (20 ml), and aluminum chloride (1.31 g) was added under ice-cooling, which was followed by stirring at room temperature for 1.5 hr. Ice water and conc. hydrochloric acid were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallized from ethyl acetate-hexane to give 0.45 g of 6-bromo-1-(2-benzo[b]thienyl)-1-hexanone.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography
  7. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a1f924a53cb34ba39f567c91b73e2460
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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