Thionyl Chloride → 3-Chloromethyl-4-trifluoromethylpyridine hydrochloride

HRID 1292045Notes

Reaction equation

HRID 1292045 reaction equation
O[CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10].O=S(Cl)[Cl:15]>C(Cl)Cl>[ClH:15].[Cl:15][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18914105(4-(Trifluoromethyl)pyridin-3-yl)methanol

Product 1

HCID 189141093-Chloromethyl-4-trifluoromethylpyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-hydroxymethyl-4-trifluoromethylpyridine (1.11 g, 6.27 mmol) from step 1 above in CH2Cl2 (20 mL) at 0° C. was added SOCl2 (0.89 g, 7.5 nmuol) in CH2Cl2 (10 mL). The mixture was allowed to warm to room temperature and stirred for 1 h, and the solvent and excess SOCl2 were evaporated under reduced pressure. The residue was concentrated from cyclohexane (3-) to give 3-chloromethyl-4-trifluoromethylpyridine hydrochloride as a solid which was used in the next step without purification (TLC: Rf = 0.75 (1:1 hexane:EtOAc)).

Workup

  1. customthe solvent and excess SOCl2 were evaporated under reduced pressure
  2. concentrationThe residue was concentrated from cyclohexane (3-)

Sources & evidence

ORD record
ord-3b1727e7aa734dc2aa105832989948a8
Source dataset
uspto-grants-1998_05
Patent number
US05756497

Reaction notes

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