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

HRID 515702Notes

Reaction equation

HRID 515702 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-e28a33fe663c4753bad9dfceb09b1502
Source dataset
uspto-grants-2015_08
Patent number
US09108969B2

Reaction notes

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