Ammonium Chloride → 4,4,4-Trifluoro-1-(4'-(trifluoromethyl)biphenyl-4-yl)butan-1-ol

Temperatur

-78 °C

n-Butyllithium (150 uL of a 2.5M solution in hexanes, 0.38 mmol) was added dropwise to a −78° C. solution of 4-bromo-4′-(trifluoromethyl)biphenyl (113 mg, 0.375 mmol) in 3 mL THF. The resulting solution was stirred at −78° C. 15 min. 4,4,4-trifluorobutyraldehyde (98 mg, 0.78 mmol) was added neat. The resulting colorless solution was stirred at −78° C. 20 min. 1 mL sat. aqueous NH4Cl was added, and the mixture warmed to room temperature. The reaction mixture was partitioned between Et2O and water. The organic layer was dried over MgSO4 and concentrated to give a colorless oil. The crude material was purified by silica gel chromatography to provide 4,4,4-trifluoro-1-(4′-(trifluoromethyl)biphenyl-4-yl)butan-1-ol (87 mg, 67%). 1H NMR (400 MHz, CDCl3) δ 7.64-7.71 (m, 4H), 7.57-7.62) m, 2H), 7.41-7.47 (m, 2H), 4.78-4.87 (m, 1H), 2.10-2.39 (m, 3H), 1.96-2.09 (m, 1H).

1. custom15 min
2. stirringThe resulting colorless solution was stirred at −78° C
3. custom20 min
4. temperaturethe mixture warmed to room temperature
5. customThe reaction mixture was partitioned between Et2O and water
6. dry with materialThe organic layer was dried over MgSO4
7. concentrationconcentrated
8. customto give a colorless oil
9. customThe crude material was purified by silica gel chromatography

ORD-Eintrag

ord-a2b996d1301e49c295667e673c03534f

Quelldatensatz

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09056834B2