反应详情

温度

0 °C

BH3 (1M in THF, 250 mL, 250 mmol) was added dropwise to a cooled sol. of 3,5-dichloro-4-hydroxybenzoic acid (20 g, 96.6 mmol) in THF (200 mL) at 0° C. The resulting mixture was stirred at 0° C. for 15 min., and then at rt for 13 h. The milky mixture was cooled to 0° C., and MeOH (150 mL), then water (100 mL), were added dropwise. The mixture was further stirred at 0° C. for 15 min, and then at rt for 5 h. The mixture was then partially concentrated under reduced pressure. EtOAc (200 mL) and water (50 mL) were added to the residue, and the phases were shaken and separated. The aq. phase was further extracted with EtOAc. The combined org. extracts were washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. Purification by FC(CH2Cl2/CH3OH, 100:1) led to the title compound as a slightly beige solid (17.86 g, 96%). LC-MS: tR=0.69 min.

1. waitat rt for 13 h
2. temperatureThe milky mixture was cooled to 0° C.
3. stirringThe mixture was further stirred at 0° C. for 15 min
4. waitat rt for 5 h
5. concentrationThe mixture was then partially concentrated under reduced pressure
6. additionEtOAc (200 mL) and water (50 mL) were added to the residue
7. stirringthe phases were shaken
8. customseparated
9. extractionThe aq. phase was further extracted with EtOAc
10. washextracts were washed with brine
11. dry with materialdried over MgSO4
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customPurification by FC(CH2Cl2/CH3OH, 100:1)