Boron trifluoride etherate → HCID 13290019, compound

HRID 652631Notes

Reaction equation

HRID 652631 reaction equation
[Cl:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]2[CH:9](O)[CH:8]([CH:11]([CH3:13])[CH3:12])[S:7][C:6]=2[C:14]=1[Cl:15].B(F)(F)F.CCOCC.[OH-].[Na+]>C(O)(=O)C.O>[Cl:1][C:2]1[C:3]([O:16][CH3:17])=[CH:4][C:5]2[CH:9]=[C:8]([CH:11]([CH3:12])[CH3:13])[S:7][C:6]=2[C:14]=1[Cl:15]

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 14798Sodium Hydroxide2×HCID 13290178HCID 13290178, compound

Product 1

HCID 13290019HCID 13290019, compoundYield 35.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To 28.4 g of 6,7-dichloro-2,3-dihydro-3-hydroxy-2-isopropyl-5-methoxybenzo[b]thiophene in 139 ml of glacial acetic acid is added 35 ml of boron trifluoride etherate. The reaction is heated on a steam bath for 10 minutes and allowed to stir at room temperature for 90 min. The reaction is poured into a mixture of 250 ml of 10% sodium hydroxide solution and 150 ml of ice. The mixture is basified with 50% sodium hydroxide solution, diluted with 600 ml of water and extracted with four 300 ml-portions of ether. The combined ether extracts are washed with one 350 ml-portion of water, one 150 ml-portion of saturated sodium chloride solution and dried over magnesium sulfate to give 26.4 g of a clear, brown oil of high purity by thin-layer chromatography. A 10 g-portion of the oil is chromatographed on 500 ml of silica gel with ether:hexane (1:2) to give 9.55 g of 6,7-dichloro-2-isopropyl-5-methoxybenzo[b]thiophene as a clear, colorless oil which solidified to a low melting solid, mp <37°, pure by thin-layer chromatography (silica gel, 1:1, ether-hexane or carbon tetrachloride).

Workup

  1. temperatureThe reaction is heated on a steam bath for 10 minutes
  2. extractionextracted with four 300 ml-portions of ether
  3. washThe combined ether extracts are washed with one 350 ml-portion of water, one 150 ml-portion of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customto give 26.4 g of a clear, brown oil of high purity by thin-layer chromatography
  6. customA 10 g-portion of the oil is chromatographed on 500 ml of silica gel with ether:hexane (1:2)

Sources & evidence

ORD record
ord-f6eab89e7c314b879c70b59119ed5a22
Source dataset
uspto-grants-1987_06
Patent number
US04672138

Reaction notes

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