Diiodomethane → HCID 22568990, compound

Temperature

-40 °C

To a solution of 2,4,6-trichlorophenol (1.90 g, 9.64 mmol) in methylene chloride (70 ml) at −40° C. was added diethyl zinc (9.64 ml, 1M solution in hexane, 9.64 mmol). The mixture was stirred at −40° C. for 20 min and then CH2I2 (778 μl, 9.64 mmol) was added. After stirring for an additional 20 min, 1-bromo-4-(1-methoxyvinyl)-benzene (1.37 g, 6.43 mmol) was added. The reaction mixture was slowly warmed to rt and stirring was continued for 16 h. Pentane was added and the mixture was washed with 1M HCl, sat. NaHCO3, sat. Na2SO3 and brine. The organic layer was dried (MgSO4), filtered, concentrated in vacuo to give a crude residue which was purified by flash column chromatography (2% ethylacetate in cyclohexane-10% ethylacetate in cyclohexane) to give 1-bromo-4-(1-methoxycyclopropyl)-benzene (880 mg, 60%) as a yellow oil. 1H NMR (CDCl3, 300 MHz): δ 7.46 (d, J=8.5 Hz, 2H), 7.18 (d, J=8.5 Hz, 2H), 3.21 (s, 3H), 1.21-1.17 (m, 2H), 0.95-0.91 (m, 2H).

1. stirringAfter stirring for an additional 20 min
2. temperatureThe reaction mixture was slowly warmed to rt
3. stirringstirring
4. waitwas continued for 16 h
5. washthe mixture was washed with 1M HCl, sat. NaHCO3, sat. Na2SO3 and brine
6. dry with materialThe organic layer was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give a crude residue which
10. customwas purified by flash column chromatography (2% ethylacetate in cyclohexane-10% ethylacetate in cyclohexane)

ORD record

ord-d39757e1e8cd46a09c2724b41744932d

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07259183B2