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

HRID 706693Notes

Reaction equation

HRID 706693 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9]O)=[N:7][CH:8]=1.O=S(Cl)[Cl:15]>C(Cl)Cl>[ClH:15].[Cl:15][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:12])([F:11])[F:1])=[CH:8][N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3820787(5-(Trifluoromethyl)pyridin-2-yl)methanol

Product 1

HCID 686914462-(Chloromethyl)-5-(trifluoromethyl)pyridine hydrochlorideYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of (5-(trifluoromethyl)pyridin-2-yl)methanol (0.400 g, 2.26 mmol) in CH2Cl2 (4.4 mL) was cooled to 0° C. and SOCl2 (0.494 mL, 6.77 mmol) was added as a CH2Cl2 solution (2.2 mL). The reaction was allowed to gradually warm to ambient temperature over 1 hour and then stirred for an additional 1 hour. The reaction was concentrated and dried under vacuum to provide the desired product (0.520 g, 99%) as dark oil that was used directly in the subsequent step.

Workup

  1. concentrationThe reaction was concentrated
  2. customdried under vacuum

Sources & evidence

ORD record
ord-d8a5388716484d558e875b22ad5b8f8e
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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