Diiodomethane → HCID 59557748, compound

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).

1. additionthe reaction mixture was poured slowly into ice cold dilute hydrochloride solution
2. stirringwith stirring
3. extractionThe mixture was extracted with ethyl acetate (3×10 mL)
4. washThe combined organic layers were washed with water (10 mL)
5. dry with materialwith brine (10 mL), and then dried over sodium sulfate
6. concentrationThe residue was concentrated
7. custompurified by preparative TLC (eluent EA:PE=1:25)
8. customto obtain intermediate CR (86 mg) as a light yellow oil

ORD record

ord-1aefd59d2e2a4bd4b9abf51b63e8d57e

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08106021B2