HCID 86701454, compound → HCID 86701455, compound
Reaction equation
[CH3:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][C:5]([C:6]#[N:7])=[C:4]([S:13][CH3:14])[CH:3]=1.[CH:15]([Mg]Br)=[CH2:16]>C1COCC1>[CH3:1][C:2]1[C:9]2[NH:10][CH:16]=[CH:15][C:8]=2[C:5]([C:6]#[N:7])=[C:4]([S:13][CH3:14])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 4-methyl-2-(methylthio)-5-nitrobenzonitrile (1.6 g, 7.68 mmol) in THF (80 mL) at −78° C. under nitrogen, was added rapidly 1M vinylmagnesium bromide in THF (30.7 mL, 30.7 mmol). After addition was complete, the reaction was stirred at −78° C. for 30 min. The reaction was then quenched with sat. aq. NH4Cl and extracted with EtOAc. The organic extract was dried over MgSO4, filtered and concentrated. The pure title compound was isolated using FCC (0-50% EtOAc in heptanes). MS (ESI−) m/z 201.2 (M−H).