1: 1 M HCl / 3 h / 3 °C 2: 70.6 percent / triethylamine / acetonitrile; pentane / 1.) from 0 deg C to 5 deg C, 17 min., 2.) room temp., 20 h. 3: 2 N tertiobutyllithium / diethyl ether; pentane / 0.2 h / -70 °C 4: 2.) 1 N HCl / 1.) ether, -30 deg C, 70 min., 2.) -60 deg C, 10 deg C, 1h. View Scheme

N-bromosuccinmide in methanol; water T=3°C;

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2: K2CO3 / Heating 3: (i) Br2, NaOAc, MeOH, (ii) /BRN= 3592982/ View Scheme