2'-Bromo-4-chlorophenylacetic acid methyl ester

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:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 102 g (0.55 mole) of methyl (4-chlorophenyl)acetate in 100 ml of carbon tetrachloride was added 97.9 g (0.55 mole) of N-bromosuccinimide. The resulting mixture was refluxed and irradiated with a 500 W bromo lamp for 5 hours. It was then cooled, filtered, and the filtrate was evaporated to dryness to give 150 g (103% yield) of methyl (4-chlorophenyl)bromoacetate. The resulting mixture was refluxed irradiated with a 500 W bromo lamp for 5 hours It was then cooled filtered the filtrate was evaporated to dryness

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

Procedure: To a solution of 102 g (0.55 mole) of methyl (4-chlorophenyl)acetate in 100 ml of carbon tetrachloride was added 97.9 g (0.55 mole) of N-bromosuccinimide. The resulting mixture was refluxed and irradiated with a 500 W bromo lamp for 5 hours. It was then cooled, filtered, and the filtrate was evaporated to dryness to give 150 g (103% yield) of methyl (4-chlorophenyl)bromoacetate. The resulting mixture was refluxed irradiated with a 500 W bromo lamp for 5 hours It was then cooled filtered the filtrate was evaporated to dryness

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

Procedure: To a solution of imidazole (170 mg) and triethylamine (350 ml) in DMF (1 ml), a solution of methyl 2-bromo-2-(4-chlorophenyl)-acetate (657 mg) in DMF (3 ml) was added. After stirring for an overnight, water was added to the reaction liquid, followed by extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate. The reaction liquid was condensed under reduced pressure and the resulting residue was purified on silica gel column chromatography (methanol/chloroform=1/10) to provide methyl 2-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-acetate (400 mg) as a yellow oily substance. followed by extraction with ethyl acetate washing with saturated brine drying over anhydrous sodium sulfate The reaction liquid condensed under reduced pressure the resulting residue was purified on silica gel column chromatography (methanol/chloroform=1/10)

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

Procedure: To a solution of 2,6-diallyl-4-benzyloxyphenol (200 mg, 1.0 eq) in DMF (8 mL) were added methyl α-bromo-4-chlorobenzeneacetate (190 mg, 1.0 eq) and Cs2CO3 (285 mg, 1.2 eq). The reaction mixture was stirred at room temperature for 15 h, poured into ether, washed with water and brine, dried over MgSO4, filtered, and concentrated in vac. Purification by chromatography (SiO2, EtOAc/Hexanes 1:20) afforded the desired methyl α-(2,6-diallyl-4-hydroxyphenoxy)-4-chlorobenzeneacetate. washed with water and brine dried over MgSO4 filtered concentrated in vac Purification by chromatography (SiO2, EtOAc/Hexanes 1:20)

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

Procedure: To a solution of 1-amino-2-naphthalenethiol (27.81 g) in ethanol (500 ml) is added sodium borohydride (11.35 g) at room temperature. The mixture is stirred for 20 minutes, and thereto is added dropwise acetic acid (200 ml) and is further added sodium acetate (24.6 g). To the mixture is further added dropwise methyl α-bromo-4-chlorophenylacetate (46.8 g), and the mixture is sitrred at room temperature under argon overnight. The reaction mixture is poured into ice water and the resulting precipitate is separated by filtration, washed, dried and recrystallized from tetrahydrofuran-n-hexane to give 3-(4-chlorophenyl)-1H-naphtho-[2,1-b][1,4]thiazin-2(3H)-one (44.45 g, yield 82.6%) as crystals. the mixture is sitrred at room temperature under argon overnight the resulting precipitate is separated by filtration washed dried recrystallized from tetrahydrofuran-n-hexane

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

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 imidazole (170 mg) and triethylamine (350 ml) in DMF (1 ml), a solution of methyl 2-bromo-2-(4-chlorophenyl)-acetate (657 mg) in DMF (3 ml) was added. After stirring for an overnight, water was added to the reaction liquid, followed by extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate. The reaction liquid was condensed under reduced pressure and the resulting residue was purified on silica gel column chromatography (methanol/chloroform=1/10) to provide methyl 2-(4-chlorophenyl)-2-(1H-imidazol-1-yl)-acetate (400 mg) as a yellow oily substance. followed by extraction with ethyl acetate washing with saturated brine drying over anhydrous sodium sulfate The reaction liquid condensed under reduced pressure the resulting residue was purified on silica gel column chromatography (methanol/chloroform=1/10)