Thionyl Chloride → 4-(chloromethyl)-1-isopropyl-5-(trifluoromethyl)-1H-pyrazole

HRID 82226Notes

Reaction equation

HRID 82226 reaction equation
S(Cl)([Cl:3])=O.[CH:5]([N:8]1[C:12]([C:13]([F:16])([F:15])[F:14])=[C:11]([CH2:17]O)[CH:10]=[N:9]1)([CH3:7])[CH3:6]>C(Cl)Cl>[Cl:3][CH2:17][C:11]1[CH:10]=[N:9][N:8]([CH:5]([CH3:7])[CH3:6])[C:12]=1[C:13]([F:16])([F:15])[F:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66436594(1-Isopropyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

Product 1

HCID 664366344-(chloromethyl)-1-isopropyl-5-(trifluoromethyl)-1H-pyrazoleYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (5.26 mL, 72 mmol) was added to [1-isopropyl-5-(trifluoromethyl)-1H-pyrazol-4-yl]methanol (Preparation 183, 7.5 g, 36 mmol) in DCM (75 mL) at 0° C. and the mixture was stirred for 2 hours. The mixture was diluted with DCM (30 mL) and the organic phase was washed with water (75 mL), brine (75 mL) and dried over sodium sulphate. The filtrate was evaporated in vacuo to afford 4-(chloromethyl)-1-isopropyl-5-(trifluoromethyl)-1H-pyrazole in 86% yield, 7 g.

Workup

  1. washthe organic phase was washed with water (75 mL), brine (75 mL)
  2. dry with materialdried over sodium sulphate
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-db770f9f3e0041fb8531c2a83e9ab379
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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