Dimethylformamide → 5-Chloromethyl-2-(3-trifluoromethyl-phenyl)-pyridine

HRID 33512Notes

Reaction equation

S(Cl)([Cl:3])=O.CN(C)C=O.[F:10][C:11]([F:27])([F:26])[C:12]1[CH:13]=[C:14]([C:18]2[N:23]=[CH:22][C:21]([CH2:24]O)=[CH:20][CH:19]=2)[CH:15]=[CH:16][CH:17]=1>ClCCl>[Cl:3][CH2:24][C:21]1[CH:20]=[CH:19][C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([F:27])([F:26])[F:10])[CH:13]=2)=[N:23][CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

911 mg (0.56 ml, 7.66 mmol) thionyl chloride were added drop by drop at 0° C. to a solution of 0.2 ml N,N-dimethylformamide (DMF) and 970 mg (3.83 mmol) [6-(3-Trifluoromethyl-phenyl)-pyridine-3-yl]-methanol in 30 ml dichloromethane, stirred for 5 min. at 0° C., and at r.t. for 1 h. The mixture is 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), and evaporated. Purification by chromatography on silica (eluent: ethyl acetate/n-heptane 1:3) gave 750 mg (72%) of 5-Chloromethyl-2-(3-trifluoromethyl-phenyl)-pyridine as light yellow crystals

Workup

waitat r.t. for 1 h
additionThe mixture is 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
customPurification by chromatography on silica (eluent: ethyl acetate/n-heptane 1:3)

Sources & evidence

ORD record: ord-d6c9e3c17fa240de9127e0949efdfbda
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429605B2

Reaction notes

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