Boron tribromide → 5-Formyl-5,6,7,8-tetrahydronaphthalene-1-carbonitrile
Reaction equation
C[O:2][CH:3]=[C:4]1[CH2:13][CH2:12][CH2:11][C:10]2[C:9]([C:14]#[N:15])=[CH:8][CH:7]=[CH:6][C:5]1=2.B(Br)(Br)Br>C(Cl)Cl>[CH:3]([CH:4]1[CH2:13][CH2:12][CH2:11][C:10]2[C:9]([C:14]#[N:15])=[CH:8][CH:7]=[CH:6][C:5]1=2)=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 5-(methoxymethylene)-5,6,7,8-tetrahydronaphthalene-1-carbonitrile (320 mg, 1.61 mmol) in DCM (7 mL) was added BBr3 (1.2 g, 4.8 mmol) dropwise at −78° C. under N2, then the mixture was stirred at this temperature for 3 h. It was poured into ice-saturated NaHCO3 solution, and extracted with DCM. The organic layer was washed with brine and dried over Na2SO4. The solvent was removed in vacuo to give crude title compound, which was used for next step.