1: With n-butyllithium; boric acid trimethyl ester 2: With hydrogenchloride

magnesium in tetrahydrofuran

hydrogenchloride in tetrahydrofuran; hexane

1.1: 100 percent / K2CO3 2.1: trimethyl borate; n-butyllithium 2.2: 100 percent / aq. HCl View Scheme

1.1: 100 percent / K2CO3 2.1: trimethyl borate; n-butyllithium 2.2: 100 percent / aq. HCl View Scheme

n-butyllithium in tetrahydrofuran N2; BuLi dropping into org. compd. soln. at -78°C, mixt. keeping 3 h, B-compd. soln. addn. dropwise at -78°C, mixt. allowing to warm to room temp. overnight , stirring 1 h with 10percent HCl, extn. (Et2O); org. extracts washing (water), drying, solvent vac. removal;

1: 81 percent / aq. Na2CO3; Pd(PPh3)4 / benzene / 4 h / Heating 2: 63 percent / BBr3 / benzene / 2 h / Heating View Scheme

tetrakis(triphenylphosphine) palladium(0); sodium carbonate