1,2-Dimethoxyethane → 2-Cyano-4'-methylbiphenyl

Participants

Reaction Steps

A suspension of MnCl2 (0.25 g, 1.98 mmol) and LiCl (0.17 g, 3.955 mmol) in a mixture of 2 ml of anhydrous tetrahydrofuran and 0.38 ml of dimethoxyethane (3.955 mmol) is stirred at room temperature. After stirring for approximately 30 minutes, a homogeneous medium is obtained. The addition is then so carried out of 1/1: PdCl2/dppp (0.023 g, 1 mol %) and of o-bromobenzonitrile (0.72 g, 3.955 mmol) and then a solution of p-tolylmagnesium chloride in tetrahydrofuran (1.80N, 2.86 ml, 5.14 mmol) is added over 2 hours at room temperature. After stirring for 90 minutes, the reaction mixture is treated as described in Example 1. The o-(p-tolyl)benzonitrile is thus obtained with a yield of isolated product of 95%.

Provenance & Evidence