Diiodomethane → 4-Bromo-1-chloro-2-(4-(cyclopropoxymethyl)benzyl)benzene

To a stirred mixture of 4-bromo-1-chloro-2-(4-(vinyloxymethyl)benzyl)benzene (0.7 g, 2.07 mmol) and Et2Zn (5.18 mL, 5.18 mmol, 1.0 M in hexane) in dry ethyl ether (10 mL) was added diiodomethane (0.42 mL, 5.18 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 (3×20 mL). The combined organic layers were washed with water (20 mL) and then with brine (20 mL), and then dried over sodium sulfate. The residue was concentrated and purified by column chromatography (eluent EA:PE=1:200) to obtain intermediate CV (0.6 g) as a colorless oil. 1H NMR (CDCl3, 400 MHz): δ 7.33˜7.24 (m, 5H), 7.18 (d, 2H), 4.55 (s, 2H), 4.07 (s, 2H), 3.40˜3.37 (m, 1H), 0.69˜0.49 (m, 4H).

1. additionthe reaction mixture was poured slowly into ice cold dilute hydrochloride solution
2. stirringwith stirring
3. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
4. washThe combined organic layers were washed with water (20 mL)
5. dry with materialwith brine (20 mL), and then dried over sodium sulfate
6. concentrationThe residue was concentrated
7. custompurified by column chromatography (eluent EA:PE=1:200)
8. customto obtain intermediate CV (0.6 g) as a colorless oil

ORD-Eintrag

ord-f942c7f83c854e97a9c30141ccd66123

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08106021B2