methyl 2-phenylsulfanylacetate

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

Procedure: A solution of methyl thiophenoxyacetate (60g.) in methylene chloride (100ml.) was added over 20 minutes to a stirred suspension of chloroacetyl chloride (45.2g.) and aluminium chloride (134g.) in methylene chloride (400ml.) at room temperature. The resulting solution was stirred at room temperature overnight and poured onto a mixture of ice (2kg.) and concentrated hydrochloric acid (50ml.). This mixture was then stirred at room temperature for 1 hour. The methylene chloride phase was separated, dried (MgSO4) and evaporated in vacuo. The residue was recrystallised from methanol to give methyl 4-(chloroacetyl)-thiophenoxyacetate (60.1g.), m.p. 61°-63° C. This mixture was then stirred at room temperature for 1 hour The methylene chloride phase was separated dried (MgSO4) evaporated in vacuo The residue was recrystallised from methanol

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

Procedure: A room temperature solution of (phenylsulfanyl)acetic acid (8.4 g, 50.0 mmol) in methanol (100 mL) was treated with chlorotrimethylsilane (13 mL, 100.0 mmol), stirred for 16 hours, and concentrated. The concentrate was dissolved in 5:1/hexanes:diethyl ether, filtered through a pad of silica gel (80 g), rinsed with 5:1/hexanes:diethyl ether, and concentrated to provide the desired product. concentrated The concentrate was dissolved in 5:1/hexanes diethyl ether, filtered through a pad of silica gel (80 g) rinsed with 5:1/hexanes diethyl ether, and concentrated

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

Procedure: A room temperature solution of (phenylsulfanyl)acetic acid (8.4 g, 50.0 mmol) in methanol (100 mL) was treated with chlorotrimethylsilane (13 mL, 100.0 mmol), stirred for 16 hours, and concentrated. The concentrate was dissolved in 5:1/hexanes:diethyl ether, filtered through a pad of silica gel (80 g), rinsed with 5:1/hexanes:diethyl ether, and concentrated to provide the desired product. concentrated The concentrate was dissolved in 5:1/hexanes diethyl ether, filtered through a pad of silica gel (80 g) rinsed with 5:1/hexanes diethyl ether, and concentrated

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

Procedure: A room temperature solution of (phenylsulfanyl)acetic acid (8.4 g, 50.0 mmol) in methanol (100 mL) was treated with chlorotrimethylsilane (13 mL, 100.0 mmol), stirred for 16 hours, and concentrated. The concentrate was dissolved in 5:1/hexanes:diethyl ether, filtered through a pad of silica gel (80 g), rinsed with 5:1/hexanes:diethyl ether, and concentrated to provide the desired product. concentrated The concentrate was dissolved in 5:1/hexanes diethyl ether, filtered through a pad of silica gel (80 g) rinsed with 5:1/hexanes diethyl ether, and concentrated

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

Procedure: A room temperature solution of (phenylsulfanyl)acetic acid (8.4 g, 50.0 mmol) in methanol (100 mL) was treated with chlorotrimethylsilane (13 mL, 100.0 mmol), stirred for 16 hours, and concentrated. The concentrate was dissolved in 5:1/hexanes:diethyl ether, filtered through a pad of silica gel (80 g), rinsed with 5:1/hexanes:diethyl ether, and concentrated to provide the desired product. concentrated The concentrate was dissolved in 5:1/hexanes diethyl ether, filtered through a pad of silica gel (80 g) rinsed with 5:1/hexanes diethyl ether, and concentrated