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With ammonia; ammonium chloride; In methanol; water; at 20℃; for 2h;
To a solution of NaCN (0.99 g, 19.7 mmol), NH4Cl (1.06 g, 19.7 mmol) in ammonium hydroxide (28%, 10 mL) was added a solution of <strong>[189628-39-5]3-fluoro-5-methylbenzaldehyde</strong> (1.36 g, 9.85 mmol) in methanol (5 mL). The mixture was stirred at rt for 2 h. The solvents EPO <DP n="36"/>were removed by vacuum evaporation. To the residue was added 6 N HCl (8 mL) and the mixture was heated at reflux for 90 min. The solvents were removed by vacuum evaporation. To the residue was added dry THF (25 mL) followed by BH3-THF complex (1.0 M in THF, 30 mL, 30.0 mmol). The mixture was heated at reflux for 2 h. After cooling, methanol (8 mL) was added and the mixture was refluxed for another 15 min. The solvents were evaporated under reduced pressure. The residue was diluted with saturated aqueous NaHCO3 (30 mL), extracted with 5:1 CHCl3-Z-PrOH (3 x 200 mL). The extracts were dried over Na2SO4 and the solvents were evaporated to give the crude product. This was purified by silica gel column chromatography (95:4:1, CH2Cl2/MeOH/NH4OH) to give 2-amino-2-(2-fluoro-5-methyl- phenyl)-ethanol (984 mg, 59%).
With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20℃; for 1h;
[0484j BF3.OEt2 (2.61 ml, 21.16 mmol) was added dropwise to a solution of 1,3-propanedithiol (2.48 ml, 24.47 mmol) and <strong>[189628-39-5]3-fluoro-5-methylbenzaldehyde</strong> (3.38 g, 24.47 mmol) in DCM (122 ml) at 0 C. The reaction was stirred at ambient temperature for 1 hour where TLC (5% EtOAc/hexane) indicated a complete reaction. The reaction mixture was then diluted with DCM (100 ml), filtered through Celite (and the Celite pad was washed with additional DCM (3 x 100 ml)) and the filtrate washed with brine (100 ml), saturated NaHCO3 (3 x 100 ml), 10% KOH solution (100 ml), water (100 ml) and brine (100 ml) and finally dried over sodium sulfate. The organic extract was filtered and evaporated to afford 2-(3-fluoro-5-methylphenly)-1,3-dithiane (4.69 g, 77%) as a light pink solid. The productwas used in the next step without further purification. The NMR was consistent with the proposed structure.
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