2-Amino-5-iodobenzonitrile → 2-Amino-5-benzylbenzonitrile

Participants

Reaction Steps

(DPPF)PdCl2—CH2Cl2 (82 mg, 0.1 mmol) was added to 0.5 M benzylzinc bromide in dry THF (10 mL, calculated to contain 5 mmol), and the mixture was stirred at room temperature for 5 min under N2. A solution of 9 (488 mg, 2 mmol) in dry THF (2 mL) was then added, and the reaction was heated under reflux and monitored by TLC (silica gel, 2:1 CH2Cl2-hexanes). After 30 min the reaction was quenched by addition of saturated aqueous NH4Cl (10 mL) followed by saturated aqueous Na2EDTA (10 mL), and stirring was continued for another 30 min. The brown mixture was extracted several times with CH2Cl2, and the combined extracts were washed with brine, dried over Na2SO4, and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (2:1 CH2Cl2-hexanes) to obtain 2-amino-5-benzylbenzonitrile (10a) as a white powder (210 mg, 51%): mp 68-69° C.; 1H NMR (DMSO-d6) δ 3.75 (s, 2H, CH2), 5.85 (br s, 2H, NH2), 6.70 (d, J=8 Hz, 1H, H-3), 7.13-7.26 (m, 7H, aromatic protons). The product was used directly in the next reaction (Step 3).

Provenance & Evidence