1-fluoro-3-methylsulfanylbenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-fluoro-3-(methylsulfanyl)benzene (1.98 g, 14.0 mmol) and 4-chlorobutyryl chloride in CH2Cl2 (15 mL) was added AlCl3 (2.06 g, 15.4 mmol) at 20° C. under N2. The reaction mixture was stirred for 15 h at 20° C. for 12 h then quenched by addition of H2O and extracted with Et2O. The combine organic solution was washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting white solid was recrystalized to give 4-chloro-1-[4-fluoro-2-(methylsulfanyl)phenyl]-1-butanone (2.80 g, 81%) as a white needle shape crystal. then quenched by addition of H2O extracted with Et2O The combine organic solution was washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The resulting white solid was recrystalized

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-fluorothiophenol (4.73 g, 37.0 mmol) in diethyl carbonate (11 mL, 129 mmol) was added K2CO3 (7.67 g, 55.5 mmol) and 18-crown-6 ether (100 mg, 0.37 mmol). The reaction mixture was refluxed at 100° C. for 12 h. The reaction mixture was cooled to 20° C. then quenched by addition of H2O and extracted with Et2O. The combine organic solution was washed with H2O and brine, dried over MgSO4.to give 1-fluoro-3-(methylsulfanyl)benzene (5.10 g, 97%) as a colorless oil. The reaction mixture was cooled to 20° C. then quenched by addition of H2O extracted with Et2O The combine organic solution was washed with H2O and brine dried over MgSO4

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-fluoro-3-(methylsulfanyl)benzene (1.98 g, 14.0 mmol) and 4-chlorobutyryl chloride in CH2Cl2 (15 mL) was added AlCl3 (2.06 g, 15.4 mmol) at 20° C. under N2. The reaction mixture was stirred for 15 h at 20° C. for 12 h then quenched by addition of H2O and extracted with Et2O. The combine organic solution was washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting white solid was recrystalized to give 4-chloro-1-[4-fluoro-2-(methylsulfanyl)phenyl]-1-butanone (2.80 g, 81%) as a white needle shape crystal. then quenched by addition of H2O extracted with Et2O The combine organic solution was washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The resulting white solid was recrystalized

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-fluorothiophenol (4.73 g, 37.0 mmol) in diethyl carbonate (11 mL, 129 mmol) was added K2CO3 (7.67 g, 55.5 mmol) and 18-crown-6 ether (100 mg, 0.37 mmol). The reaction mixture was refluxed at 100° C. for 12 h. The reaction mixture was cooled to 20° C. then quenched by addition of H2O and extracted with Et2O. The combine organic solution was washed with H2O and brine, dried over MgSO4.to give 1-fluoro-3-(methylsulfanyl)benzene (5.10 g, 97%) as a colorless oil. The reaction mixture was cooled to 20° C. then quenched by addition of H2O extracted with Et2O The combine organic solution was washed with H2O and brine dried over MgSO4

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-fluoro-3-(methylsulfanyl)benzene (1.98 g, 14.0 mmol) and 4-chlorobutyryl chloride in CH2Cl2 (15 mL) was added AlCl3 (2.06 g, 15.4 mmol) at 20° C. under N2. The reaction mixture was stirred for 15 h at 20° C. for 12 h then quenched by addition of H2O and extracted with Et2O. The combine organic solution was washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting white solid was recrystallized to give 4-chloro-1-[4-fluoro-2-(methylsulfanyl)phenyl]-1-butanone (2.80 g, 81%) as a white needle shape crystal. then quenched by addition of H2O extracted with Et2O The combine organic solution was washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The resulting white solid was recrystallized

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-fluorothiophenol (4.73 g, 37.0 mmol) in diethyl carbonate (11 mL, 129 mmol) was added K2CO3 (7.67 g, 55.5 mmol) and 18-crown-6 ether (100 mg, 0.37 mmol). The reaction mixture was refluxed at 100° C. for 12 h. The reaction mixture was cooled to 20° C. then quenched by addition of H2O and extracted with Et2O. The combine organic solution washed with H2O and brine, dried over MgSO4 to give 1-fluoro-3-(methylsulfanyl)benzene (5.10 g, 97%) as a colorless oil. The reaction mixture was cooled to 20° C. then quenched by addition of H2O extracted with Et2O The combine organic solution washed with H2O and brine dried over MgSO4

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-fluoro-3-(methylsulfanyl)benzene (1.98 g, 14.0 mmol) and 4-chlorobutyryl chloride in CH2Cl2 (15 mL) was added AlCl3 (2.06 g, 15.4 mmol) at 20° C. under N2. The reaction mixture was stirred for 15 h at 20° C. for 12 h then quenched by addition of H2O and extracted with Et2O. The combine organic solution was washed with H2O and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting white solid was recrystalized to give 4-chloro-1-[4-fluoro-2-(methylsulfanyl)phenyl]-1-butanone (2.80 g, 81%) as a white needle shape crystal. then quenched by addition of H2O extracted with Et2O The combine organic solution was washed with H2O and brine dried over MgSO4 filtered concentrated in vacuo The resulting white solid was recrystalized