Thionyl Chloride → 2-Vinylphenyl 4-(trifluoromethyl)benzenesulfonate

HRID 1795121Notes

Reaction equation

HRID 1795121 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]=O)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:23][Si](C[Mg]Cl)(C)C.S(Cl)(Cl)=O>C1COCC1.C(OCC)C>[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]=[CH2:23])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 221856712-Formylphenyl 4-(trifluoromethyl)benzenesulfonateHCID 178418680HCID 178418680, compound

Product 1

HCID 221855252-Vinylphenyl 4-(trifluoromethyl)benzenesulfonate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A dry, air-free, ice-cold solution of 2-formylphenyl 4-(trifluoromethyl)-benzenesulfonate (2.0 g, 6.1 mmol) in THF (7 mL) is treated with 6.8 mL of 1 M (trimethylsilylmethyl)magnesium chloride in diethyl ether. The reaction is stirred 30 minutes. Thionyl chloride (0.5 mL, 6.9 mmol) is added and the reaction is stirred at 0° C. for 1 h. The reaction is quenched with ice and extracted with ethyl acetate. The product is purified on silica gel in methylene chloride. A yield of 1.8 g of 2-vinylphenyl 4-(trifluoromethyl)benzenesulfonate is obtained.

Workup

  1. stirringthe reaction is stirred at 0° C. for 1 h
  2. customThe reaction is quenched with ice
  3. extractionextracted with ethyl acetate
  4. customThe product is purified on silica gel in methylene chloride

Sources & evidence

ORD record
ord-84ce38934f834ca39bf43d1ded9572ce
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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