(2-bromo-4-fluorophenyl) acetate

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol (0.3 g, 1.90 mmol), sodium hydrogen carbonate (0.22 g, 2.58 mmol), 2-bromo-4-fluorophenyl acetate (0.3 g, 1.29 mmol), palladium acetate (14 mg, 0.06 mmol) and CYTOP 216, 2,4,6 trioxy 1,3,5,7 tetramethyl 8 phosphaadamantane (19 mg, 0.06 mmol) were suspended in DMF (5 ml) under nitrogen. The reaction mixture was stirred at 120° C. for 19 h, cooled to 25° C. and then diluted with ethyl acetate (20 ml) and demi water (20 ml). The phases were separated and the organic layer dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to dryness. The crude reaction mixture was then purified by flash chromatography on silica (heptane:ethyl acetate 9:1) and 6-fluoro-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2H-chromene was isolated as a pale yellow oil (60 mg, 19% yield). cooled to 25° C. The phases were separated the organic layer dried over anhydrous magnesium sulfate filtered concentrated under vacuum to dryness The crude reaction mixture was then purified by flash chromatography on silica (heptane:ethyl acetate 9:1)

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol (0.3 g, 1.90 mmol), sodium hydrogen carbonate (0.22 g, 2.58 mmol), 2-bromo-4-fluorophenyl acetate (0.3 g, 1.29 mmol), palladium acetate (14 mg, 0.06 mmol) and CYTOP 216, 2,4,6 trioxy 1,3,5,7 tetramethyl 8 phosphaadamantane (19 mg, 0.06 mmol) were suspended in DMF (5 ml) under nitrogen. The reaction mixture was stirred at 120° C. for 19 h, cooled to 25° C. and then diluted with ethyl acetate (20 ml) and demi water (20 ml). The phases were separated and the organic layer dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to dryness. The crude reaction mixture was then purified by flash chromatography on silica (heptane:ethyl acetate 9:1) and 6-fluoro-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2H-chromene was isolated as a pale yellow oil (60 mg, 19% yield). cooled to 25° C. The phases were separated the organic layer dried over anhydrous magnesium sulfate filtered concentrated under vacuum to dryness The crude reaction mixture was then purified by flash chromatography on silica (heptane:ethyl acetate 9:1)