Thionyl Chloride → 2,6-Difluoro-4-methoxybenzonitrile
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
Product 1
Reagents, catalysts & solvents 1
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
- additionpoured onto ice-water
- extractionThe product was extracted into ether (twice), and the combined ethereal extracts
- washwere washed with water, saturated sodium hydrogen carbonate, water
- dry with materialdried (MgSO4)
- customThe solvent was removed in vacuo
- 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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