4,5-dichlorobenzene-1,2-diol

反応条件: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of 4,5-dichlorocatechol (1 g, 5.62 mmol), potassium carbonate (780 mg, 5.62 mmol), and methyl iodide (0.34 mL, 5.62 mmol) in N,N-dimethylformamide (20 mL) was stirred rapidly at 130° C. for 20 hours, under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature before diluting with ethyl acetate (50 mL). The mixture was washed with water (50 mL), saturated aqueous sodium bicarbonate (50 mL), and saturated brine solution (50 mL). The organic layer was separated and dried over sodium sulphate, and evaporated under reduced pressure to a deep brown solid. The crude material was purified by flash chromatography (eluting with 1:1 heptane/dichloromethane) to afford 4,5-dichloro-2-methoxyphenol as a white solid (490 mg, 45%). to cool to room temperature The mixture was washed with water (50 mL), saturated aqueous sodium bicarbonate (50 mL), and saturated brine solution (50 mL) The organic layer was separated dried over sodium sulphate evaporated under reduced pressure to a deep brown solid The crude material was purified by flash chromatography (eluting with 1:1 heptane/dichloromethane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of sodium hydride (60% wt. disp. in oil, 0.223 g) and 4,5-dichlorocatechol (1 g) in DMF (10 ml) was stirred at RT for 15 min. tert-Butyl-bromoacetate (0.9 ml) was added, stirred at RT for 2 h then potassium carbonate (0.77 g) and the product from example 7 step (ii) (0.7 g) added and the mixture heated at 90° C. for 14 h. The mixture was partitioned between 2M sodium hydroxide solution and diethylether, the aqueous layer was acidified with 2M hydrochloric acid and extracted with ethylacetate. The ethylacetate layer was dried, evaporated under reduced pressure and the residue purified by RPHPLC. Yield 0.349 g. was added the mixture heated at 90° C. for 14 h The mixture was partitioned between 2M sodium hydroxide solution and diethylether extracted with ethylacetate The ethylacetate layer was dried evaporated under reduced pressure the residue purified by RPHPLC

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of sodium hydride (60% wt. disp. in oil, 0.223 g) and 4,5-dichlorocatechol (1 g) in DMF (10 ml) was stirred at RT for 15 min. tert-Butyl-bromoacetate (0.9 ml) was added, stirred at RT for 2 h then potassium carbonate (0.77 g) and the product from example 7 step (ii) (0.7 g) added and the mixture heated at 90° C. for 14 h. The mixture was partitioned between 2M sodium hydroxide solution and diethylether, the aqueous layer was acidified with 2M hydrochloric acid and extracted with ethylacetate. The ethylacetate layer was dried, evaporated under reduced pressure and the residue purified by RPHPLC. Yield 0.349 g. was added the mixture heated at 90° C. for 14 h The mixture was partitioned between 2M sodium hydroxide solution and diethylether extracted with ethylacetate The ethylacetate layer was dried evaporated under reduced pressure the residue purified by RPHPLC