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

HRID 1753095Notes

Reaction equation

HRID 1753095 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 105, 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 (86%, 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-efdd3a57644747e7936caf1e9d47950e
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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