p-Diiodobenzene → HCID 131723385, compound

HRID 2228393Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][CH:3]=1.[CH2:9]([Li])[CH2:10][CH2:11]C.[CH2:14]([Si:17](Cl)(C)[CH3:18])C=C>C1COCC1>[CH2:9]([C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[SiH:17]([CH3:18])[CH3:14])[CH:10]=[CH2:11]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution 1,4-diiodobenzene (16.5 g, 50 mmol) in dried THF (250 mL) at −78° C. was added n-butyllithium (22 mL, 2.5 M solution in hexanes, 55 mmol) over a period of 30 min. After being stirred for 10 min at −78° C., allylchlorodimethylsilane (6.7 g, 50 mmol) in was added dropwise over a period of 20 min, and the reaction mixture was warmed to room temperature. After stirring for 1 h at room temperature the reaction mixture was concentrated, and the residue was extracted with ether and brine. The organic layer was dried (Na2SO4) and distilled (Kugelrohr) under reduced pressure to provide a liquid (11.5 g, 76%); 1H NMR (300 MHz, CDCl3) δ 0.32 (s, 6 H), 1.78 (d, J=7.5 Hz, 2 H), 4.89 (m, 1 H), 4.92 (d, J=4.0 Hz, 1 H), 5.78 (m, 1 H), 7.27 (d, J=7.5 Hz, 2 H), 7.74 (d, J=7.5 Hz, 2 H); 13C NMR (75 MHz, CDCl3) −3.5, 23.8, 114.1, 134.4, 135.6, 137.1, 138.3, 139.6; HRMS calcd for C11H15ISi 301.9987, found 301.9990.

Workup

temperaturethe reaction mixture was warmed to room temperature
stirringAfter stirring for 1 h at room temperature the reaction mixture
concentrationwas concentrated
extractionthe residue was extracted with ether and brine
dry with materialThe organic layer was dried (Na2SO4)
distillationdistilled (Kugelrohr) under reduced pressure

Sources & evidence

ORD record: ord-8cbada41ccef4eda84ac905b4a24ec5d
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06416861B1

Reaction notes

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