反应详情

温度

70 °C

Add dropwise potassium tert-butoxide in THF (34.6 mL, 34.6 mmol) to a solution of p-bromofluorobenzene (6.1 g, 34.6 mmol) in THF (144 mL) and 3-hydroxy-azetidine-1-carboxylic acid tert-butyl ester (5.0 g, 28.9 mmol) at RT. Heat the mixture at 70° C. overnight. Cool the mixture to RT, quench with water, dilute with Et2O, and wash once with saturated NH4Cl. Back extract the aqueous with Et2O, dry the combined organics over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography, eluting with 25% EtOAc/hexane to give 4.4 g (46%) of the title compound. LC-MS/ES m/z (81Br) 274 [M−tertBu+H]+.

1. temperatureCool the mixture to RT
2. customquench with water
3. additiondilute with Et2O
4. washwash once with saturated NH4Cl
5. extractionBack extract the aqueous with Et2O
6. dry with materialdry the combined organics over Na2SO4
7. filtrationfilter
8. concentrationconcentrate
9. customPurify the crude material by flash chromatography
10. washeluting with 25% EtOAc/hexane