Carbon Tetrachloride → 5-(Chloromethyl)-2-norbornene

A mixture of triphenylphosphine (20.98 g, 0.08 mol) and bicyclo[2.2.1]hept-5-ene-2-methanol (5.0 g, 0.0403 mol) in dry carbon tetrachloride (31.5 ml) was stirred and heated at 60° for 6 h. After cooling, the reaction mixture was filtered, and the filtrate was evaporated under reduced pressure to afford a semi-crystalline mass, which was triturated with n-pentane (100 ml). The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to afford a yellow oil. Distillation of the oil afforded 5-chloromethylbicyclo[2.2.1]hept-2-ene as a colourless oil, b.p. 70°-72°/24 mm Hg.

1. temperatureheated at 60° for 6 h
2. temperatureAfter cooling
3. filtrationthe reaction mixture was filtered
4. customthe filtrate was evaporated under reduced pressure
5. customto afford a semi-crystalline mass, which
6. customwas triturated with n-pentane (100 ml)
7. filtrationThe reaction mixture was filtered
8. concentrationthe filtrate was concentrated under reduced pressure
9. customto afford a yellow oil
10. distillationDistillation of the oil

ORD-Eintrag

ord-be5eb4217c3549afb8add1c38eeb7427

Quelldatensatz

uspto-grants-1985_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04525475