Boron trifluoride etherate → HCID 13290035, compound

HRID 1903480Notes

Reaction equation

HRID 1903480 reaction equation
[CH:1]1([CH:7]2[S:11][C:10]3[C:12]([Cl:19])=[C:13]([Cl:18])[C:14]([O:16][CH3:17])=[CH:15][C:9]=3[CH:8]2O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(F)(F)F.CCOCC.[OH-].[Na+]>C(O)(=O)C>[Cl:18][C:13]1[C:14]([O:16][CH3:17])=[CH:15][C:9]2[CH:8]=[C:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[S:11][C:10]=2[C:12]=1[Cl:19]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 14798Sodium Hydroxide2×HCID 13290181HCID 13290181, compound

Product 1

HCID 13290035HCID 13290035, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 14.7 g of 2-cyclohexyl-6,7-dichloro-2,3-dihydro-3-hydroxy-5-methoxybenzo[b]thiophene, 90 ml of glacial acetic acid and 21 ml of boron trifluoride etherate is warmed on a steam bath until it becomes homogeneous and then stirred for one hour. To the reaction mixture is added 100 ml of cold 10% sodium hydroxide solution. The mixture is further basified with 50% sodium hydroxide solution and extracted with three 230 ml-portions of ether. The organic extracts are dried over anhydrous magnesium sulfate, filtered and evaporated. Recrystallization of the residue from ether-hexane gives 9.0 g of 6,7-dichloro-2-cyclohexyl-5-methoxybenzo[b]thiophene as off-white crystals, mp 60°.

Workup

  1. temperatureis warmed on a steam bath until it
  2. extractionextracted with three 230 ml-portions of ether
  3. dry with materialThe organic extracts are dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customRecrystallization of the residue from ether-hexane

Sources & evidence

ORD record
ord-c5b4fe5c09084e829bc5194d542a746f
Source dataset
uspto-grants-1984_03
Patent number
US04436748

Reaction notes

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