2-(2-Hydroxyethyl)pyridine → 2-(2-Chloroethyl)pyridine

HRID 332160Notes

Reaction equation

HRID 332160 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8]O.O=S(Cl)[Cl:12]>C(Cl)Cl>[Cl:12][CH2:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

4

Reactant 2

HCID 76752-(2-Hydroxyethyl)pyridineHCID 24386Thionyl Chloride

Product 1

HCID 1994682-(2-Chloroethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(Pyridin-2-yl)ethanol (1 g, 8.12 mmol) was first treated with SOCl2 (3 ml) in CH2Cl2 (10 ml) at rt for 3 hrs. The solvent was removed to get a crude 2-(2-chloroethyl)pyridine. Then following General Procedure A, the title compound (1.69 g, 79%) was prepared from 2-amino-4-chlorobenzenethiol (1.6 g, 9.74 mmol), K2CO3 (3.36 g, 24.36 mmol) in DMF (20 ml).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-3aa0fdd955c24a93a593eeba40de6a24
Source dataset
uspto-grants-2014_11
Patent number
US08877804B2

Reaction notes

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