cyclohexane 2 h; Dean-Stark;

1: triethylamine / tetrahydrofuran / 1.) from 0 deg C to room temp.; 2.) 20 min., room temp. 2: 1.) Ph3P.HBr; 2.) triethylamine / 1.) dichloromethane, room temp., 20 min; 2.) hexane-dichloromethane 3: aq. NaOH / methanol / 0.83 h / Ambient temperature 4: 1.) NBS; 2.) triethylamine / 1.) CD3CN, MeOH, 10 min, NMR tube; 2.) CD3CN, MeOH, NMR tube View Scheme

acetic acid in acetonitrile-D3; water

toluene-4-sulfonic acid Heating;

N-bromosuccinmide; triethylamine 1.) CD3CN, MeOH, 10 min, NMR tube; 2.) CD3CN, MeOH, NMR tube; Yield given. Multistep reaction. Yields of byproduct given;

1: 78 percent / (i-Pr)3Al / toluene; CH2Cl2 / -78 deg C to room temp., then 12 h 2: 50 percent Spectr. / AcOH / H2O; CD3CN View Scheme