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