Dimethylformamide → 3-Chloromethyl-5-(4-trifluoromethoxy-phenyl)-pyridine

HRID 33529Notes

Reaction equation

S(Cl)([Cl:3])=O.CN(C)C=O.[F:10][C:11]([F:28])([F:27])[O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]([CH2:25]O)[CH:22]=[N:23][CH:24]=2)=[CH:15][CH:14]=1>ClCCl>[Cl:3][CH2:25][C:21]1[CH:22]=[N:23][CH:24]=[C:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][C:11]([F:28])([F:27])[F:10])=[CH:14][CH:15]=2)[CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

136 mg (0.083 ml, 1.14 mmol) thionyl chloride were added drop by drop at 0° C. to a solution of 0.1 ml N,N-dimethylformamide (DMF) and 153 mg (0.57 mmol) [5-(4-Trifluoromethoxy-phenyl)-pyridin-3-yl]-methanol in 10 ml dichloromethane and stirred for 2 h at 0° C. The mixture was poured on ice/sodium bicarbonate solution and the organic phase separated. The water phase is extracted with dichloromethane. The combined organic phases were washed with water, dried (sodium sulphate), evaporated and the obtained material (156 mg, 89%) used without further purification.

Workup

additionThe mixture was poured on ice/sodium bicarbonate solution
customthe organic phase separated
extractionThe water phase is extracted with dichloromethane
washThe combined organic phases were washed with water
dry with materialdried (sodium sulphate)
customevaporated
customthe obtained material (156 mg, 89%) used without further purification

Sources & evidence

ORD record: ord-71c7f54f53f94a33a4c52385eeadf0b6
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429605B2

Reaction notes

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