Methanol → HCID 118272362, compound

HRID 590822Notes

Reaction equation

HRID 590822 reaction equation
Br[CH2:2][C:3]1[N:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:4]=1[C:5]#[N:6].[CH3:13][OH:14]>F[B-](F)(F)F.[Ag+]>[Cl:12][C:7]1[C:4]([C:5]#[N:6])=[C:3]([CH2:2][O:14][CH3:13])[N:10]=[C:9]([Cl:11])[CH:8]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 118272051HCID 118272051, compound

Product 1

HCID 118272362HCID 118272362, compound

Reagents, catalysts & solvents 1

HCID 159722Silver tetrafluoroborateCatalyst

Conditions

Temperature
50 °C

Procedure

A solution of 2-(bromomethyl)-4,6-dichloronicotinonitrile (378.9 mg, 1.425 mmol) in MeOH (5.0 ml) was charged with silver(I) tetrafluoroborate (360 mg, 1.849 mmol) and stirred at 50° C. for 17 hr. LCMS showed conversion to the desired mass. The mixture was concentrated in vacuo and purified via flash chromatography (15-60% Et2O/Hexane) to provide 4,6-dichloro-2-(methoxymethyl)nicotinonitrile. MS ESI calc'd for C8H7C12N2O [M+H]+ 217. found 217.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified via flash chromatography (15-60% Et2O/Hexane)

Sources & evidence

ORD record
ord-711572d846ed431abc596b8cf0ac6517
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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