Thionyl Chloride → HCID 66883686, compound

HRID 241380Notes

Reaction equation

HRID 241380 reaction equation
[CH:1]([C:4]1[C:8]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:7]=2[S:6][C:5]=1[CH2:17]O)([CH3:3])[CH3:2].S(Cl)([Cl:21])=O>C1C=CC=CC=1>[Cl:21][CH2:17][C:5]1[S:6][C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:8]=2[C:4]=1[CH:1]([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66883283HCID 66883283, compound

Product 1

HCID 66883686HCID 66883686, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 3-isopropyl-6-(trifluoromethyl)-benzothiophene-2-methanol (obtained in Example 12(4), 878 mg, 3.20 mmol) in benzene (27 mL) was added dropwise a solution of thionyl chloride (0.28 mL, 3.8 mmol) in benzene (5 mL) under cooling with ice. The mixture was stirred for 3 hours at room temperature. After the solvent was removed under reduced pressure, the residue was purified by chromatography on silica gel (hexane/ethyl acetate, 10:1) to give the titled compound as a pale yellow oil (655 mg, y. 70%).

Workup

  1. temperatureunder cooling with ice
  2. customAfter the solvent was removed under reduced pressure
  3. customthe residue was purified by chromatography on silica gel (hexane/ethyl acetate, 10:1)

Sources & evidence

ORD record
ord-c994cbca99e3452bb7cd9ca1a6291ccc
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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