1: 3-fluorobenzyl alcohol With N,N,N',N'',N''-pentamethyldiethylenetriamine; potassium tert-butylate; sec.-butyllithium in tetrahydrofuran; cyclohexane T=-75°C; 2 h; 2: carbon dioxide in tetrahydrofuran; cyclohexane Further stages.;

1: 1-fluoro-3-[(methoxymethoxy)methyl]benzene With N,N,N',N'',N''-pentamethyldiethylenetriamine; sec.-butyllithium in tetrahydrofuran; cyclohexane T=-75°C; 2 h; 2: carbon dioxide in tetrahydrofuran; cyclohexane Further stages.;

1.1: 71 percent / N-ethyldiisopropylamine / CH2Cl2 / 2 h / 25 °C 2.1: sec-butyllithium; N,N,N',N",N"-pentamethyldiethylenetriamine / tetrahydrofuran; cyclohexane / 2 h / -75 °C 2.2: 15 percent / tetrahydrofuran; cyclohexane View Scheme

lithium hydroxide; lithium borohydride 1.) THF, MeOH, H2O, 0 deg C to r.t.; 2.) THF; Yield given. Multistep reaction. Yields of byproduct given;