Thionyl Chloride → 2-(5-(Chloromethyl)pyridin-2-yl)benzonitrile

HRID 1440462Notes

Reaction equation

HRID 1440462 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])=[N:7][CH:8]=1.O=S(Cl)[Cl:19]>O1CCOCC1.CCOCC.[Cl-].[Cl-].[Zn+2]>[Cl:19][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])=[N:7][CH:8]=1

Participants

6

Reactant 2

HCID 24386Thionyl ChlorideHCID 100360172-(5-(Hydroxymethyl)pyridin-2-yl)benzonitrile

Product 1

HCID 99913952-(5-(Chloromethyl)pyridin-2-yl)benzonitrileYield 94%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.), stirred solution of 2-[5-(hydroxymethyl)pyridin-2-yl]benzonitrile (4.3 g, 0.020 mol) and ZnCl2 (0.09 g, 0.61 mmol) in p-dioxane (40 mL) was added SOCl2 (1.50 mL, 0.020 mol) dropwise. The mixture was stirred at room temperature for 18 h, diluted with ether, washed with water and brine, dried (MgSO4), and concentrated to give 4.30 g (92%) of product as a brown solid, mp 97°-98° C.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f5efed1e01364d1b8134c6bd04f3e6bc
Source dataset
uspto-grants-1996_03
Patent number
US05498776

Reaction notes

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