Thionyl Chloride → 2-(Chloromethyl)-5-(trifluoromethyl)pyridine

HRID 1160221Notes

Reaction equation

HRID 1160221 reaction equation
[ClH:1].[F:2][C:3]([F:13])([F:12])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10]O)=[N:8][CH:9]=1.O=S(Cl)[Cl:16]>>[Cl:16][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([F:13])([F:12])[F:2])=[CH:9][N:8]=1.[ClH:1].[Cl:16][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([C:3]([F:13])([F:12])[F:2])=[CH:9][N:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 68694003(5-(trifluoromethyl)pyridin-2-yl)methanol HCl salt

Product 2

HCID 183617202-(Chloromethyl)-5-(trifluoromethyl)pyridineHCID 686914462-(Chloromethyl)-5-(trifluoromethyl)pyridine hydrochloride

Procedure

The mixture of (5-(trifluoromethyl)pyridin-2-yl)methanol HCl salt (293 mg, 1.4 mmol) and SOCl2 (1.5 ml) was stirred for 10 min. After this time, the solution was concentrated under reduced pressure to give the title compound, 2-(chloromethyl)-5-(trifluoromethyl)pyridine HCl salt.

Workup

  1. concentrationAfter this time, the solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-35205fb3e7a441dd9cf647040934d051
Source dataset
uspto-grants-2010_10
Patent number
US07816357B2

Reaction notes

Loading…