Potassium Hydroxide → Benzene, 1-bromo-3-(4,4,4-trifluorobutyl)-

Temperature

100 °C

A mixture of 1-(3-bromo-phenyl)-4,4,4-trifluoro-butan-1-one (3.1 g, 11 mmol) and diglyme was treated with hydrazine mono hydrate (5.5 g, 110.3 mmol), and stirred at 100° C. for 2 hours then treated with powder KOH (3.1 g, 55.1 mmol). The stirring continued at 150° C. for 6 hours. The mixture was cooled to room temperature, poured into a mixture of ice/water and extracted with ethyl ether. The extracts were combined, dried over MgSO4 and concentrated in vacuo. The crude product was purified on silica gel (ISCO) using hexanes as the eluting solvent to give 1-Bromo-3-(4,4,4-trifluoro-butyl)-benzene as a colorless oil (2.4 g, 88% yield). m/e (M)+ 266; 1H NMR (400 MHZ, DMSO-d6) δ ppm, 1.7-1.8 (m, 2 H), 2.1-2.2 (m, 2 H), 2.6 (t, J=7.6 Hz, 2 H), 7.2-7.25 (m, 2 H), 7.3-7.35 (m, 1 H), 7.4 (s, 1 H)

1. waitThe stirring continued at 150° C. for 6 hours
2. temperatureThe mixture was cooled to room temperature
3. extractionextracted with ethyl ether
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo
6. customThe crude product was purified on silica gel (ISCO)

ORD record

ord-6b4269c9fbc04ff79ff751fdddd84e67

Source dataset

uspto-grants-2008_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07423158B2