5-[2-(2-Chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one → 5-[2-(2-Chloro-4-hydroxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:28])[C:11]([C:17]1[CH:18]=[CH:19][C:20]2[O:24][C:23](=[O:25])[N:22]([CH3:26])[C:21]=2[CH:27]=1)([OH:16])[C:12]([F:15])([F:14])[F:13]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:28])[C:11]([C:17]1[CH:18]=[CH:19][C:20]2[O:24][C:23](=[O:25])[N:22]([CH3:26])[C:21]=2[CH:27]=1)([OH:16])[C:12]([F:13])([F:14])[F:15]Komponenten
3
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
5-[2-(2-Chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3-methyl-3H-benzooxazol-2-one (766 mg) was dissolved in CH2Cl2 (25 mL) and cooled to −78° C. Borontribromide (1M in CH2Cl2, 7.37 mL) was added over a period of 20 minutes. Stirring was continued for 1.5 hours at −78° C. The cooling bath was removed and the mixture was allowed to warm to 0° C. Stirring was continued for 2 hours at 0° C. The reaction mixture was poured into ice and basified with sat. NaHCO3 and extracted three times with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4, filtered and the solvent was evaporated. The title compound was obtained as a colorless foam (740 mg, 99%) and was used without further purification. MS (m/e)=402.2 [M+H+].