Thionyl Chloride → 4-(Chloromethyl)-1-(fluoromethoxy)-2-(trifluoromethyl)benzene

HRID 515711Notes

Reaction equation

HRID 515711 reaction equation
[F:1][CH2:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10]O)=[CH:6][C:5]=1[C:12]([F:15])([F:14])[F:13].S(Cl)([Cl:18])=O>>[Cl:18][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([O:3][CH2:2][F:1])=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:6]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 67250584(4-(Fluoromethoxy)-3-(trifluoromethyl)phenyl)methanol

Product 1

HCID 668477234-(Chloromethyl)-1-(fluoromethoxy)-2-(trifluoromethyl)benzeneYield 80.3%

Procedure

(4-(Fluoromethoxy)-3-(trifluoromethyl)phenyl)methanol (1.84 g, 8.21 mmol) was dissolved in thionyl chloride (8.09 mL, 111 mmol) and stirred for 3 h. The reaction was taken up in hexanes and washed with water (twice), saturated NaHCO3, and water. The organics were dried over MgSO4, filtered and concentrated under vacuum to give the title compound as a solid (1.60 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.83 (s, 2H), 5.83-6.14 (d, J=53.1 Hz, 2H), 7.46 (d, J=8.46 Hz, 1H), 7.69-7.87 (m, 2H).

Workup

  1. washwashed with water (twice), saturated NaHCO3, and water
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b76405ddbc2a4510b29d4cdca064efb8
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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