Acetic Acid → HCID 13290076, compound

HRID 1903513Notes

Reaction equation

HRID 1903513 reaction equation
[Cl:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]2[CH2:9][CH:8]([CH2:10][CH:11]([CH3:13])[CH3:12])[S:7][C:6]=2[C:14]=1[Cl:15].C(O)(=O)C.B(F)(F)F.CCOCC.[OH-].[Na+]>ClCCl>[Cl:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH:11]([CH3:13])[CH3:12])[S:7][C:6]=2[C:14]=1[Cl:15]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8000Boron trifluoride etherateHCID 14798Sodium HydroxideHCID 20197912HCID 20197912, compound

Product 1

HCID 13290076HCID 13290076, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 18 g of 6,7-dichloro-2,3-dihydro-2-isobutyl-5-methoxybenzo[b]thiophene, 90 ml of glacial acetic acid and 25 ml of boron trifluoride etherate is heated on a steam bath until dissolution occurs and for an additional 30 mins, with stirring. The reaction mixture is poured onto ice and the mixture is basified with 25% sodium hydroxide solution and extracted with ether. The ether extracts are washed with water, sodium bicarbonate solution, water, dried and filtered. Evaporation of the filtrate affords an oil which crystallies on cooling in a dry ice-acetone bath. Chromatography of the crystalline material on alumina using dichloromethane as the eluent affords 14.5 g of 6,7-dichloro-5-methoxy-2-isobutylbenzo[b]thiophene, mp 40°-41°.

Workup

  1. temperatureis heated on a steam bath until dissolution
  2. additionThe reaction mixture is poured onto ice
  3. extractionextracted with ether
  4. washThe ether extracts are washed with water, sodium bicarbonate solution, water
  5. customdried
  6. filtrationfiltered
  7. customEvaporation of the filtrate
  8. customaffords an oil which
  9. temperatureon cooling in a dry ice-acetone bath

Sources & evidence

ORD record
ord-ab07fef93fd14a5594d37b5db7a1824f
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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