Reaktion #79266

Reaktionsgleichung

4-chloro-1,1-diphenyl-1-butene

cyclopropyl-(4-fluorophenyl)ketone

4-fluorophenyl magnesium bromide

→

1,1-Bis(4-fluorophenyl)-4-chloro-1-butene

Ausbeute 88.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched by addition of brine
2. 2
   Extraktionextracted with Et2O
3. 3
   WaschenThe organic layer was then washed with NaHCO3 saturated aqueous solution and brine
4. 4
   TrocknenIt was then dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigeto give crude bis(4-fluorophenyl)-cyclopropylmethanol
8. 8
   SonstigeIt was used for ring opening reaction
9. 9
   Sonstigewithout further purification

Vorschrift

To a solution of cyclopropyl-(4-fluorophenyl)ketone (520 mg, 3.17 mmol) in THF (10 mL) was added 4-fluorophenyl magnesium bromide dropwise at 0° C. under N2 atmosphere. The reaction mixture was stirred for 1 h at 0° C., quenched by addition of brine and extracted with Et2O. The organic layer was then washed with NaHCO3 saturated aqueous solution and brine. It was then dried over MgSO4, filtered, concentrated in vacuo to give crude bis(4-fluorophenyl)-cyclopropylmethanol. It was used for ring opening reaction by following the procedure for formation of 4-chloro-1,1-diphenyl-1-butene without further purification. 1,1-Bis(4-fluorophenyl)-4-chloro-1-butene (780 mg, 88%) was obtained as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ2.57 (q, 2H, J=6.9 Hz), 3.58 (t, 2H, J=6.9 Hz), 6.04 (t, 1H, J=7.3 Hz), 6.92-7.21 (m, 8H) ppm.

Quelle