Thionyl Chloride → 2,6-Difluoro-4-methoxybenzonitrile

HRID 466491Notes

Reaction equation

HRID 466491 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[C:11]([F:17])[C:7]=1[C:8]([NH2:10])=O>CN(C=O)C>[F:5][C:6]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[C:11]([F:17])[C:7]=1[C:8]#[N:10]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 27787702,6-Difluoro-4-methoxybenzamide

Product 1

HCID 27787722,6-Difluoro-4-methoxybenzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of thionyl chloride (139.0 g, 1.17 mol) in dry DMF (150 ml) was added to a stirred solution of compound 26 (20.0 g, 0.11 mol) in dry DMF (250 ml) at room temperature. The mixture was stirred at room temperature overnight and then poured onto ice-water. The product was extracted into ether (twice), and the combined ethereal extracts were washed with water, saturated sodium hydrogen carbonate, water and dried (MgSO4). The solvent was removed in vacuo to give off-white crystals.

Workup

  1. additionpoured onto ice-water
  2. extractionThe product was extracted into ether (twice), and the combined ethereal extracts
  3. washwere washed with water, saturated sodium hydrogen carbonate, water
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed in vacuo
  6. customto give off-white crystals

Sources & evidence

ORD record
ord-ec772511e3f64619a63fe8ef27fddd87
Source dataset
uspto-grants-1992_10
Patent number
US05156763

Reaction notes

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