trifluoroacetic acid in dichloromethane 1.5 h;

trifluoroacetic acid in chloroform Yield given;

1: 99 percent / aq. K2CO3, n-Bu4NI / tetrahydrofuran 2: 51 percent / Br2 / acetic acid / 60 °C 3: 1.) quinoline, pyridine, 2.) aq. K2CO3, n-Bu4NI / 1.) 160 deg C, 2.) CH2Cl2 4: 74 percent / NH4OAc / acetic acid 5: LiAlH4 / tetrahydrofuran / Heating 6: Et3N / CH2Cl2 7: 28 percent / 1.) Na, NH3, 2.) S2Cl2 / 2.) THF 8: TFA / CHCl3 View Scheme

1: 1.) quinoline, pyridine, 2.) aq. K2CO3, n-Bu4NI / 1.) 160 deg C, 2.) CH2Cl2 2: 74 percent / NH4OAc / acetic acid 3: LiAlH4 / tetrahydrofuran / Heating 4: Et3N / CH2Cl2 5: 28 percent / 1.) Na, NH3, 2.) S2Cl2 / 2.) THF 6: TFA / CHCl3 View Scheme

1: 51 percent / Br2 / acetic acid / 60 °C 2: 1.) quinoline, pyridine, 2.) aq. K2CO3, n-Bu4NI / 1.) 160 deg C, 2.) CH2Cl2 3: 74 percent / NH4OAc / acetic acid 4: LiAlH4 / tetrahydrofuran / Heating 5: Et3N / CH2Cl2 6: 28 percent / 1.) Na, NH3, 2.) S2Cl2 / 2.) THF 7: TFA / CHCl3 View Scheme

1: 85 percent / Br2 / acetic acid 2: 99 percent / aq. K2CO3, n-Bu4NI / tetrahydrofuran 3: 51 percent / Br2 / acetic acid / 60 °C 4: 1.) quinoline, pyridine, 2.) aq. K2CO3, n-Bu4NI / 1.) 160 deg C, 2.) CH2Cl2 5: 74 percent / NH4OAc / acetic acid 6: LiAlH4 / tetrahydrofuran / Heating 7: Et3N / CH2Cl2 8: 28 percent / 1.) Na, NH3, 2.) S2Cl2 / 2.) THF 9: TFA / CHCl3 View Scheme

1: Et3N / CH2Cl2 2: 28 percent / 1.) Na, NH3, 2.) S2Cl2 / 2.) THF 3: TFA / CHCl3 View Scheme

1: 74 percent / NH4OAc / acetic acid 2: LiAlH4 / tetrahydrofuran / Heating 3: Et3N / CH2Cl2 4: 28 percent / 1.) Na, NH3, 2.) S2Cl2 / 2.) THF 5: TFA / CHCl3 View Scheme

1: LiAlH4 / tetrahydrofuran / Heating 2: Et3N / CH2Cl2 3: 28 percent / 1.) Na, NH3, 2.) S2Cl2 / 2.) THF 4: TFA / CHCl3 View Scheme