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-bottomed flask equipped with a three-way stopcock with a vacuum line attached on one side and an ultra-dry N2 filled balloon on the other side. With this setup, the flask headspace could be readily evacuated and nitrogen gas admitted to the evacuated space. Thus, DMAC was kept under a N2 environment. To the 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 gas was allowed to enter the flask via adjustment of the 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, and the organic layer was separated and washed with saturated solution of NH4Cl. The EtOAc layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give yellow solid 7 in 89% yield by NMR.

Provenance & Evidence