Thionyl Chloride → HCID 20794543, compound

HRID 1849880Notes

Reaction equation

HRID 1849880 reaction equation
[C:1]1([CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:22])=O>>[Cl:22][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]([F:19])([F:18])[F:17])[CH:10]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 20794915HCID 20794915, compound

Product 1

HCID 20794543HCID 20794543, compoundYield 44%

Procedure

A solution of phenyl(3-(trifluoromethoxy)phenyl)methanol (300 mg, 1.12 mmol) in thionyl chloride (50 mL) was refluxed for 5 h. The solvent was removed and the residue was purified by silica gel chromatography (eluting with petroleum ether/EtOAc=100/1) to give the target compound (140 mg, 44%) as a pale yellow oil. 1H-NMR (500 MHz, DMSO-d6): δ 7.56-7.49 (m, 5H), 7.42-7.40 (m, 2H), 7.35-7.32 (m, 2H), 6.62 (m, 1H).

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by silica gel chromatography (eluting with petroleum ether/EtOAc=100/1)

Sources & evidence

ORD record
ord-76ce4158a621435f9213e7386ebeb10d
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

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