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

HRID 1526407Notes

Reaction equation

HRID 1526407 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].O=S(Cl)[Cl:19]>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 99.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (4-isopropoxy-3-(trifluoromethyl)phenyl)methanol (181 g, 773 mmol) in toluene (1 L) was added SOCl2 (338 mL, 4637 mmol) (slight exotherm to 35° C. after addition of SOCl2) and was stirred overnight in a 2-L round bottomed flask. The reaction mixture was concentrated in vacuo and diluted with hexanes (1 L). The solution was washed with sat. NaHCO3 (2×750 mL), dried over MgSO4, and filtered. The solvents were removed under reduced pressure to give 4-(chloromethyl)-1-isopropoxy-2-(trifluoromethyl)benzene (194 g, 768 mmol, 99% yield) as an orange oil. Optionally the product can be further purified by distillation (bp=85° C. at 0.1 mTorr) to obtain a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.37 (d, J=6.1 Hz, 6 H), 4.56 (s, 2H) 4.65 (sep, J=6.1 Hz, 1 H), 6.98 (d, J=8.6 Hz, 1 H), 7.48 (dd, J1=8.6, J2=2.3 Hz, 1 H), 7.57 (d, J=2.2 Hz, 1 H).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with hexanes (1 L)
  3. washThe solution was washed with sat. NaHCO3 (2×750 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-0f11e524d7704310a73ca69d974e0cb5
Source dataset
uspto-grants-2015_07
Patent number
US09085581B2

Reaction notes

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