1-fluoronaphthalen-2-ol

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1-fluoronaphthalen-2-ol (280 mg, 1.73 mmol) and K2CO3 (1.2 g, 8.65 mmol) in 10 mL of acetone, 2-bromo-2,2-difluoro-N-(furan-2-ylmethyl)acetamide (527 mg, 2.08 mmol) were added. The resulting mixture was stirred at 40° C. overnight. The reaction was cooled at room temperature, diluted with ethyl acetate (30 mL) and washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to afford 2,2-difluoro-2-[(1-fluoronaphthalen-2-yl)oxy]-N-(furan-2-ylmethyl)acetamide as red oil (650 mg) which was used in the next step without further purification. The reaction was cooled at room temperature washed with water The organic layer was dried over anhydrous sodium sulfate filtered concentrated in vacuo

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

Procedure: To a solution of 1-fluoronaphthalen-2-ol (0.162 g, 1.0 mmol) and K2CO3 (0.300 g, 2.0 mmol) in acetone was added tert-butyl (2-bromoethyl)carbamate (0.336 g, 1.5 mmol). The resulting mixture was heated at reflux overnight. After TLC control (n-hexane/ethyl acetate 6:4) showed the disappearance of 1-fluoronaphthalen-2-ol, solvent was evaporated in vacuo and the residue was dissolved in 15 mL of ethyl acetate and washed with water (3×5 mL), brine (10 mL) and dried over Na2SO4. The evaporation of solvent afforded tert-butyl {2-[(1-fluoronaphthalen-2-yl)oxy]ethyl}carbamate as a white solid (65% yield) which was used without further purification. The resulting mixture was heated at reflux overnight was evaporated in vacuo the residue was dissolved in 15 mL of ethyl acetate washed with water (3×5 mL), brine (10 mL) dried over Na2SO4 The evaporation of solvent