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

HRID 1964120Notes

Reaction equation

HRID 1964120 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11]O)=[CH:7][C:6]=1[C:13]([F:16])([F:15])[F:14])([CH3:3])[CH3:2].S(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[Cl:19][CH2:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH:1]([CH3:3])[CH3:2])=[C:6]([C:13]([F:16])([F:15])[F:14])[CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 63320666(4-Isopropoxy-3-(trifluoromethyl)phenyl)methanol

Product 1

HCID 533782354-(Chloromethyl)-1-isopropoxy-2-(trifluoromethyl)benzeneYield 92.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of (4-isopropoxy-3-(trifluoromethyl)phenyl)methanol (11.27 mmol) in toluene (20 mL) was added thionyl chloride (67.7 mmol). The reaction was stirred at 75° C. for 3 h. The mixture was diluted with hexanes, washed with water (twice), saturated NaHCO3, dried over MgSO4, and filtered. The solvent was removed under vacuum to give the title compound as an oil (10.4 mmol). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.29 (d, J=6.06 Hz, 6H), 4.75-4.85 (m, 3H), 7.30 (d, J=8.46 Hz, 1H), 7.63-7.70 (m, 2H).

Workup

  1. washwashed with water (twice), saturated NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-ed363a33faa7498cad8fd6257a6895d2
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

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