potassium hydroxide; palladium dihydroxide in ethanol; water

in diethyl ether; water

hydrogenchloride Heating;

cesium fluoride in acetonitrile Ambient temperature;

1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) up to room temp. 2: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) up to 0 deg C 3: 1) 2.3 M n-BuLi / 1) ether, -78 deg C, 5 min, 2) ether, up to room temp. 4: 89 percent / CsF / acetonitrile / Ambient temperature View Scheme

1: COCl2, DMF / CH2Cl2 / Ambient temperature 2: CH2Cl2 / Ambient temperature 3: SOCl2 / CHCl3 / Ambient temperature 4: 1) lithium diisopropylamide / 1) THF, -78 deg C, 30 min, 2) up to room temp. 5: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) up to room temp. 6: 99 percent / CsF, H2O / dimethylformamide / Ambient temperature 7: 61 percent / 6 N HCl / Heating View Scheme

1: CH2Cl2 / Ambient temperature 2: SOCl2 / CHCl3 / Ambient temperature 3: 1) lithium diisopropylamide / 1) THF, -78 deg C, 30 min, 2) up to room temp. 4: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) up to room temp. 5: 99 percent / CsF, H2O / dimethylformamide / Ambient temperature 6: 61 percent / 6 N HCl / Heating View Scheme

1: 1) 2.3 M n-BuLi / 1) ether, -78 deg C, 5 min, 2) ether, up to room temp. 2: 89 percent / CsF / acetonitrile / Ambient temperature View Scheme

1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 30 min, 2) up to room temp. 2: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) up to room temp. 3: 99 percent / CsF, H2O / dimethylformamide / Ambient temperature 4: 61 percent / 6 N HCl / Heating View Scheme

1: 1) lithium diisopropylamide / 1) THF, 0 deg C, 30 min, 2) up to room temp. 2: 99 percent / CsF, H2O / dimethylformamide / Ambient temperature 3: 61 percent / 6 N HCl / Heating View Scheme