N-bromosuccinmide; dibenzoyl peroxide in tetrachloromethane Heating;

2.1: NBS / CCl4 2.2: 82 percent / NBS; (PhCO2)2 / CCl4 View Scheme

1.1: 87 percent / benzyltriethylammonium chloride; NaOH / CH2Cl2 / 0 - 20 °C 2.1: LDA / tetrahydrofuran / 0.67 h / -30 °C 2.2: 96 percent / tetrahydrofuran / 3 h / 20 °C 3.1: 67 percent / NBS / CCl4 / 12 h / 20 °C 4.1: 82 percent / K2CO3; H2O / methanol / 6.5 h / Heating 5.1: 89 percent / LiHMDS / tetrahydrofuran / -78 - 20 °C 6.1: 91 percent / NBS; benzoyl peroxide / CCl4 / Heating View Scheme

1.1: LDA / tetrahydrofuran / 0.67 h / -30 °C 1.2: 96 percent / tetrahydrofuran / 3 h / 20 °C 2.1: 67 percent / NBS / CCl4 / 12 h / 20 °C 3.1: 82 percent / K2CO3; H2O / methanol / 6.5 h / Heating 4.1: 89 percent / LiHMDS / tetrahydrofuran / -78 - 20 °C 5.1: 91 percent / NBS; benzoyl peroxide / CCl4 / Heating View Scheme

1: 67 percent / NBS / CCl4 / 12 h / 20 °C 2: 82 percent / K2CO3; H2O / methanol / 6.5 h / Heating 3: 89 percent / LiHMDS / tetrahydrofuran / -78 - 20 °C 4: 91 percent / NBS; benzoyl peroxide / CCl4 / Heating View Scheme