反应详情

温度

70 °C

A solution of potassium tertiary-butylate (90 mg, 0.8 mmol) in tert.-butanol (1 ml, synthesis quality, 99%) was added to 2-fluoro-6-nitrotoluene (776 mg, 5 mmol) and paraformaldehyde (150 mg, 5 mmol) in DMSO (2.5 ml, synthesis quality, additionally dried for 2 d over molecular sieve 4 Å). After the addition of the potassium tertiary-butylate solution, a color change from yellow to deep violet occurred. The solution was stirred for 5 min at room temperature and for 30 min at 70° C. (oil bath temperature). It was then left to cool down to room temperature and neutralized with a few drops of conc. HCl. The mixture was diluted with EtOAc (30 ml) and washed with H2O (20 ml). The aqueous phase was post-extracted with EtOAc (2×20 ml). Drying the organic phases over Na2SO4, filtering and evaporating the solvent under reduced pressure yielded the crude product (1.11 g) which was purified by column chromatography (20 g SiO2, 12×2 cm, solvent: PE 40 ml, PE/EtOAc 10:1 110 ml, 8:1 270 ml, 6:1 210 ml, 5:1 60 ml, 4:1 50 ml). 2-(2-fluoro-6-nitrophenyl)ethanol (653 mg, 71%) was obtained as a yellow solid.

1. custom2.5 ml, synthesis quality
2. customadditionally dried for 2 d over molecular sieve 4 Å)
3. additionAfter the addition of the potassium tertiary-butylate solution
4. waitIt was then left
5. temperatureto cool down to room temperature and neutralized with a few drops of conc. HCl
6. additionThe mixture was diluted with EtOAc (30 ml)
7. washwashed with H2O (20 ml)
8. extractionThe aqueous phase was post-extracted with EtOAc (2×20 ml)
9. dry with materialDrying the organic phases over Na2SO4
10. filtrationfiltering
11. customevaporating the solvent under reduced pressure
12. customyielded the crude product (1.11 g) which
13. customwas purified by column chromatography (20 g SiO2, 12×2 cm, solvent: PE 40 ml, PE/EtOAc 10:1 110 ml, 8:1 270 ml, 6:1 210 ml, 5:1 60 ml, 4:1 50 ml)