1-iodo-2-methylsulfinylbenzene

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

Procedure: The title compound was prepared from 1-iodo-2-(methylsulfinyl)benzene (Step 1) and sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate (prepared according to the method of Example 6 Steps 1-3). 1H NMR (500 MHz, CDCl3) δ 8.61 (1H, s), 8.31 (1H, d, J=7.8 Hz), 8.21 (1H, d, J=7.8 Hz), 8.06 (1H, d, J=8.5 Hz), 8.01 (1H, s), 7.97 (1H, d, J=8.7 Hz), 7.88-7.82 (3H, m), 7.71-7.65 (3H, m), 7.19 (2H, t, J=8.6 Hz), 3.03 (3H, s); m/z (ES+) 425 [MH+]. prepared

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

Procedure: The title compound was prepared from 1-iodo-2-(methylsulfinyl)benzene (Step 1) and sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate (prepared according to the method of Example 6 Steps 1-3). 1H NMR (500 MHz, CDCl3) δ 8.61 (1H, s), 8.31 (1H, d, J=7.8 Hz), 8.21 (1H, d, J=7.8 Hz), 8.06 (1H, d, J=8.5 Hz), 8.01 (1H, s), 7.97 (1H, d, J=8.7 Hz), 7.88-7.82 (3H, m), 7.71-7.65 (3H, m), 7.19 (2H, t, J=8.6 Hz), 3.03 (3H, s); m/z (ES+) 425 [MH+]. prepared

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

Procedure: 3-Chloroperoxybenzoic acid (77%, 2.7 g, 11.99 mmol) was added to a solution of 2-iodothioanisole (3 g, 11.99 mmol) in dichloromethane (50 mL). The reaction was stirred for 1 hour. Calcium hydroxide (1.33 g, 18 mmol) was added and the mixture stirred for 15 minutes. The solid was removed by filtration through Hyflo®, washing well with dichloromethane. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 20% then 40% ethyl acetate/isohexane, to give 1-iodo-2-(methylsulfinyl)benzene as a colourless oil (2.8 g, 88%). 1H NMR (500 MHz, CDCl3) δ 7.92 (1H, d, J=7.8 Hz), 7.82 (1H, d, J=7.8 Hz), 7.62 (1H, t, J=7.6 Hz), 7.23-7.21 (1H, m), 2.79 (3H, s). the mixture stirred for 15 minutes The solid was removed by filtration through Hyflo® washing well with dichloromethane The filtrate was concentrated in vacuo The residue was purified by flash column chromatography on silica eluting with 20%

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

Procedure: The title compound was prepared from 1-iodo-2-(methylsulfinyl)benzene (Step 1) and sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate (prepared according to the method of Example 6 Steps 1-3). 1H NMR (500 MHz, CDCl3) δ 8.61 (1H, s), 8.31 (1H, d, J=7.8 Hz), 8.21 (1H, d, J=7.8 Hz), 8.06 (1H, d, J=8.5 Hz), 8.01 (1H, s), 7.97 (1H, d, J=8.7 Hz), 7.88-7.82 (3H, m), 7.71-7.65 (3H, m), 7.19 (2H, t, J=8.6 Hz), 3.03 (3H, s); m/z (ES+) 425 [MH+]. prepared

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

Procedure: 3-Chloroperoxybenzoic acid (77%, 2.7 g, 11.99 mmol) was added to a solution of 2-iodothioanisole (3 g, 11.99 mmol) in dichloromethane (50 mL). The reaction was stirred for 1 hour. Calcium hydroxide (1.33 g, 18 mmol) was added and the mixture stirred for 15 minutes. The solid was removed by filtration through Hyflo®, washing well with dichloromethane. The filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 20% then 40% ethyl acetate/isohexane, to give 1-iodo-2-(methylsulfinyl)benzene as a colourless oil (2.8 g, 88%). 1H NMR (500 MHz, CDCl3) δ 7.92 (1H, d, J=7.8 Hz), 7.82 (1H, d, J=7.8 Hz), 7.62 (1H, t, J=7.6 Hz), 7.23-7.21 (1H, m), 2.79 (3H, s). the mixture stirred for 15 minutes The solid was removed by filtration through Hyflo® washing well with dichloromethane The filtrate was concentrated in vacuo The residue was purified by flash column chromatography on silica eluting with 20%