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-d16991501e754c86808dcc151aba88c7

Quelldatensatz

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08575321B2