Reaktion #512268

Reaktionsgleichung

4-bromo-1-chloro-2-(4-(2-(vinyloxy)ethyl)benzyl)benzene

Et2Zn

diiodomethane

→

4-bromo-1-chloro-2-(4-(2-cyclopropoxyethyl)benzyl)benzene

Lösungsmittel

ethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthe reaction mixture was poured slowly into ice cold dilute hydrochloride solution
2. 2
   workup.STIRRINGwith stirring
3. 3
   ExtraktionThe mixture was extracted with ethyl acetate (3×10 mL)
4. 4
   WaschenThe combined organic layers were washed with water (10 mL)
5. 5
   Trocknenwith brine (10 mL), and then dried over sodium sulfate
6. 6
   EinengenThe residue was concentrated
7. 7
   Sonstigepurified by preparative TLC (eluent EA:PE=1:25)
8. 8
   Sonstigeto obtain intermediate CR (86 mg) as a light yellow oil

Vorschrift

To a stirred mixture of 4-bromo-1-chloro-2-(4-(2-(vinyloxy)ethyl)benzyl)benzene (100 mg, 0.27 mmol) and Et2Zn (0.68 mL, 0.68 mmol, 1.0 M in hexane) in dry ethyl ether (2 mL) was added diiodomethane (0.06 mL, 0.68 mmol) dropwise during 20 min at room temperature under argon. After stirring overnight, the reaction mixture was poured slowly into ice cold dilute hydrochloride solution with stirring. The mixture was extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (10 mL) and then with brine (10 mL), and then dried over sodium sulfate. The residue was concentrated and purified by preparative TLC (eluent EA:PE=1:25) to obtain intermediate CR (86 mg) as a light yellow oil. 1H-NMR (CDCl3, 400 MHz): δ 7.32˜7.24 (m, 3H), 7.18 (d, 2H), 7.12 (d, 2H), 4.05 (s, 2H), 3.73 (t, J=7.2 Hz, 2H), 3.32˜3.29 (m, 1H), 2.88 (t, J=7.2 Hz, 2H), 0.57˜0.44 (m, 4H).

Quelle