1-chloro-3-(2,2-dimethoxyethylsulfanyl)benzene

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

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

Procedure: To a solution of 3-chlorothiophenol (2.4 g, 16.6 mmol) in THF (200 mL) at 0° C. is added bromoacetaldehyde dimethyl acetal (2.8 g, 16.6 mmol). To the solution is added sodium hydride (0.70 g, 17.4 mmol, 60% mineral oil dispersion). The reaction is stirred for 16 hours, then quenched by the addition of saturated NH4Cl (aq.). The solution is diluted with EtOAc. The organic layer is washed with saturated NaCl (aq.). The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with hexanes. The title compound (3.7 g, 15.9 mmol) is obtained as an oil. quenched by the addition of saturated NH4Cl (aq.) The solution is diluted with EtOAc The organic layer is washed with saturated NaCl (aq.) The organic layer is dried over MgSO4 filtered concentrated The crude product is purified by column chromatography eluting with hexanes

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

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

Procedure: To a solution of 3-chlorothiophenol (2.4 g, 16.6 mmol) in THF (200 mL) at 0° C. is added bromoacetaldehyde dimethyl acetal (2.8 g, 16.6 mmol). To the solution is added sodium hydride (60% mineral oil dispersion, 0.70 g, 17.4 mmol). The reaction is stirred for 16 hours, and then is quenched by the addition of saturated NH4Cl (aq.). The solution is diluted with EtOAc. The organic layer is washed with a saturated NaCl (aq.). The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with hexanes. The title compound (3.7 g, 15.9 mmol) is obtained as an oil. 1H NMR (CDCl3, 300 MHz) δ7.32 (m, 1H), 7.25 (m, 1H), 7.12 (m, 1H), 4.47 (m, 1H), 3.07 (s, 3H), 3.02 (s, 3H). is quenched by the addition of saturated NH4Cl (aq.) The solution is diluted with EtOAc The organic layer is washed with a saturated NaCl (aq.) The organic layer is dried over MgSO4 filtered concentrated The crude product is purified by column chromatography eluting with hexanes

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

Procedure: To a solution of 3-chlorothiophenol (2.4 g, 16.6 mmol) in THF (200 mL) at 0° C. is added bromoacetaldehyde dimethyl acetal (2.8 g, 16.6 mmol). To the solution is added sodium hydride (0.70 g, 17.4 mmol, 60% mineral oil dispersion). The reaction is stirred for 16 hours, then quenched by the addition of saturated NH4Cl (aq.). The solution is diluted with EtOAc. The organic layer is washed with saturated NaCl (aq.). The organic layer is dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with hexanes. The title compound (3.7 g, 15.9 mmol) is obtained as an oil. quenched by the addition of saturated NH4Cl (aq.) The solution is diluted with EtOAc The organic layer is washed with saturated NaCl (aq.) The organic layer is dried over MgSO4 filtered concentrated The crude product is purified by column chromatography eluting with hexanes