Thionyl Chloride → 3-(Chloromethyl)-2-fluoropyridine

HRID 332165Notes

Reaction equation

HRID 332165 reaction equation
[F:1][C:2]1[C:7]([CH2:8]O)=[CH:6][CH:5]=[CH:4][N:3]=1.O=S(Cl)[Cl:12]>C(Cl)Cl>[Cl:12][CH2:8][C:7]1[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 147614612-Fluoro-3-(hydroxymethyl)pyridine

Product 1

HCID 226413043-(Chloromethyl)-2-fluoropyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2-Fluoropyridin-3-yl)methanol (508 mg, 3.998 mmol) was first treated with SOCl2 (1.5 ml) in CH2Cl2 (5 ml) at rt for 3 hrs. The solvent was removed to get a crude 3-(chloromethyl)-2-fluoropyridine. Then following General Procedure A, the title compound (910 mg, 85%) was prepared from 2-amino-4-chlorobenzenethiol (957 mg, 5.995 mmol), K2CO3 (2.7 g, 19.98 mmol) in DMF (20 ml).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-f9d46c005a5044ff84378be262ad9fc4
Source dataset
uspto-grants-2014_11
Patent number
US08877804B2

Reaction notes

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