4-Bromo-2-fluorobenzonitrile → 2-Tert-butoxy-4-bromobenzonitrile
Reaction equation
F[C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][C:12]([CH3:15])([O-:14])[CH3:13].[K+]>C1COCC1>[C:12]([O:14][C:2]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])([CH3:15])([CH3:13])[CH3:11]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-fluoro-4-bromobenzonitrile (2.0 g, 10 mmol) in 10 mL of THF, cooled to −15° C., was added a solution of potassium t-butoxide (10 mL, 10 mmol) over 7 min. The cooling bath was removed, and the reaction stirred for another 40 min. The reaction was poured into ether/10% HCl, and the ether layer was separated. The ether layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated to give 2.5 g of 2-t-butoxy-4-bromobenzonitrile.