Nitrogen → 10-Formylanthracene-9-carbonitrile

Participants

Reaction Conditions

Reaction Steps

DMAC (N,N-dimethylacetamide) was used as a solvent. As reaction is oxygen sensitive, DMAC was placed in three necked round bottom flask with three way stopcock with vacuum line in one side and ultra dry N2 balloon on the other side. Evacuation of the flask was done and DMAC was kept under N2 environment. To three necked flask Bromoaldehyde 6 (25 mg, 0.088 mmol), Zn(CN)2 (18.5 mg, 0.157 mmol), Pd2(dba)3 (2.09 mg, 0.002 mmol), Zn dust (1 mg, 0.022 mmol) were weighed out and flask was evacuated and N2 was allowed to enter the flask via three way stopcock. DMAC (4 mL) was added to the flask via a syringe keeping the flask under vacuum. t-Butyl phosphine (1.77 mg, 0.009 mmol) was added via syringe. The whole assembly was transferred in an oil bath at 80° C. and let the reaction stir at 80° C. for three hours. After monitoring the consumption of 6 by TLC (40% CH2Cl2/Hexane), EtOAc (20 mL) was added to the reaction mixture and crude reaction mixture was washed with saturated solution of K2CO3, organic layer was again washed with saturated solution of NH4Cl. The EtOAc layer was dried over anhydrous Na2SO4, filtered and removed in vacuo to give yellow solid 7 in 89% yield by NMR.

Provenance & Evidence