Benzyl Bromide → 4-Benzyloxy-5-(4-fluorophenoxy)-1-pentene

Temperatur

25 °C

A solution of 5-(4-fluorophenoxy)-1-penten-4-ol (9.81 g., 0.05 mole) in dry dimethylformamide (15 ml.) is added dropwise to a stirred suspension of hexane (2 × 10 ml.)--prewashed sodium hydride (50% dispersion in mineral oil, 2.64 g., 0.055 mole) in dry dimethylformamide (45 ml.) at 25° C. Upon cessation of gas evolution, the reaction mixture is cooled to 0°-5° C. and treated with a solution of benzyl bromide (10.3 g., 0.06 mole) in dry dimethylformamide (10 ml.). The resulting mixture is stirred at 25° C. for 16 hours, then heated at 100° C. for 1 hour. After cooling to 25° C., the reaction mixture is diluted with ice water (50 ml.) and extracted with ether four times. The combined organic extract is washed with 2 N hydrochloric acid and saturated aqueous brine, dried over magnesium sulfate and filtered. In vacuo evaporation of the filtrate leaves an oily residue which affords the title compound upon distillation as a colorless oil (13.1 g., 92%), bp0.025 112°-116° C.; pmr (CCl4) δ2.37 (2H, t), 3.5-4.0 (3H, m), 4.57 (2H, s), 4.8-5.05 (H, m), 5.05-5.25 (H, m), 5.4-6.2 (H, m), 6.6-7.1 (4H, m) and 7.19 (5H, s).

1. customat 25° C
2. temperatureUpon cessation of gas evolution, the reaction mixture is cooled to 0°-5° C.
3. temperatureheated at 100° C. for 1 hour
4. temperatureAfter cooling to 25° C.
5. extractionextracted with ether four times
6. extractionThe combined organic extract
7. washis washed with 2 N hydrochloric acid and saturated aqueous brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. customIn vacuo evaporation of the filtrate
11. customleaves an oily residue which

ORD-Eintrag

ord-2b9ed2ca36b14e29a8b280b667b0512f

Quelldatensatz

uspto-grants-1978_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04102888