1: With n-butyllithium in tetrahydrofuran T=-78°C; 1 h; 2: With boric acid trimethyl ester in tetrahydrofuran T=-78 - 20°C; Further stages.;

n-butyllithium in tetrahydrofuran to N-(2-bromobenzyl)-N-methyl-m-tolylamine in THF at -78°C was added n-BuLi in THf, stirred at -78°C for 1 h, added to THF soln. B(OMe)3 at -78°C under Ar, allowed to warm to room temp.; HCl was added and stirred for 1 h, water was added, aq. phase wasextd. with CH2Cl2, organic layers were combined and dried over MgSO4, solvent was removed in vacuo;

1.1: 98 percent / K2CO3 / acetonitrile / 4 h / Heating 2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 2.2: 25 percent / B(OCH3)3 / tetrahydrofuran / -78 - 20 °C View Scheme

1.1: 98 percent / K2CO3 / acetonitrile / 4 h / Heating 2.1: n-BuLi / tetrahydrofuran / 1 h / -78 °C 2.2: 25 percent / B(OCH3)3 / tetrahydrofuran / -78 - 20 °C View Scheme