1: 50 percent / 1.) n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 40 min, 2.) -78 deg C, 15 min then RT, 2 h 2: 1.) BBr3, 2.) 2 M NaOH, air / 1.) CH2Cl2, 0 deg C, 30 min then RT, overnight, 2.) RT, 4 h View Scheme

1: 70 percent / tetrahydrofuran; diethyl ether / 1.) -15 deg C, 15 min, 2.) RT, 1 h 2: anisole / CH2Cl2 / 3 h 3: 50 percent / 1.) n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 40 min, 2.) -78 deg C, 15 min then RT, 2 h 4: 1.) BBr3, 2.) 2 M NaOH, air / 1.) CH2Cl2, 0 deg C, 30 min then RT, overnight, 2.) RT, 4 h View Scheme

1: 50 percent / 1.) n-BuLi / tetrahydrofuran; hexane / 1.) -78 deg C, 40 min, 2.) -78 deg C, 15 min then RT, 2 h 2: 1.) BBr3, 2.) 2 M NaOH, air / 1.) CH2Cl2, 0 deg C, 30 min then RT, overnight, 2.) RT, 4 h View Scheme

sodium hydroxide; air; boron tribromide 1.) CH2Cl2, 0 deg C, 30 min then RT, overnight, 2.) RT, 4 h; Yield given. Multistep reaction;