Thionyl Chloride → HCID 86761826, compound

HRID 2090987Notes

Reaction equation

HRID 2090987 reaction equation
[CH:1]1([CH:7]([C:9]2[S:10][C:11]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:12]=3[CH:13]=2)O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:24])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:24][CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:9]1[S:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:12]=2[CH:13]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 86761827HCID 86761827, compound

Product 1

HCID 86761826HCID 86761826, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of cyclohexyl[5-(trifluoromethyl)-1-benzothiophen-2-yl]methanol (860 mg) synthesized above in toluene (20 mL) was added thionyl chloride (239 μL), and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was poured into ice-cooled saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (806 mg, 89%) as a pale-brown oil

Workup

  1. additionThe reaction mixture was poured into ice-
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a5459a9e80144f888bb4dd69f374e4ea
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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