Thionyl Chloride → HCID 67358175, compound

HRID 2385095Notes

Reaction equation

HRID 2385095 reaction equation
[F:1][C:2]1[C:3]([CH2:9]O)=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.S(Cl)([Cl:13])=O>ClCCl.CN(C)C=O>[ClH:13].[Cl:13][CH2:9][C:3]1[C:2]([F:1])=[CH:7][C:6]([F:8])=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 53414314(3,5-Difluoropyridin-2-YL)methanol

Product 1

HCID 67358175HCID 67358175, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3,5-difluoropyridin-2-yl)methanol (Almedia et al., WO 08/117,050) (2.15 g, 14.8 mmol) in dichloromethane (20 mL) at 0° C. was added N,N-dimethylformamide (2 drops) and thionyl chloride (2.0 mL, 27 mmol). The solution was stirred at ambient temperature for 1 h and concentrated in vacuo to afford 2-(chloromethyl)-3,5-difluoropyridine hydrochloride (2.31 g, 78%) as a brown oil: Rf=0.71 (EtOAc/Hexanes, 1/1).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f1722a5202de42b78b3807b2850185a6
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

Loading…