Chloroiodomethane → 1-(Cyclopropyloxy)-2-iodo-4-(trifluoromethoxy)benzene

HRID 1267886Notes

Reaction equation

[CH:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[I:15])=[CH2:2].Cl[CH2:17]I.C([Zn]CC)C>ClCCCl>[CH:1]1([O:3][C:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]([F:12])([F:13])[F:14])=[CH:6][C:5]=2[I:15])[CH2:17][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

1-(Vinyloxy)-2-iodo-4-(trifluoromethoxy)benzene (Description 11; 7.6 g, 23 mmol) and chloroiodomethane (5.4 mL, 74 mmol) were dissolved in 1,2-dichloroethane (40 mL) and cooled to 0° C. Diethyl zinc (3.8 mL, 36.8 mmol) was then added dropwise. The solution was allowed to warm to room temperature for 10 minutes, then cooled back to 0° C. when it was quenched with saturated aqueous ammonium chloride solution (50 mL). The suspension formed was extracted with 50% diethyl ether/hexane (2×100 mL) and the extracts dried (MgSO4). Concentration yielded a yellow oil which was purified by silica chromatography to give the title compound as a clear oil (5.84 g, 17 mmol).

Workup

temperatureto warm to room temperature for 10 minutes
temperaturecooled back to 0° C. when it
customwas quenched with saturated aqueous ammonium chloride solution (50 mL)
customThe suspension formed
extractionwas extracted with 50% diethyl ether/hexane (2×100 mL)
dry with materialthe extracts dried (MgSO4)
concentrationConcentration
customyielded a yellow oil which
customwas purified by silica chromatography

Sources & evidence

ORD record: ord-4badb6081cae49b19b8e7bc10685ad2a
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06555552B2

Reaction notes

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