Benzene, 1,3-diiodo- → HCID 68108894, compound

Participants

Reaction Steps

A solution of 1,3-diiodobenzene (3.0 g, 9.09 mmol) in dry THF (40 mL) was cooled to −78° C. under a nitrogen before addition of n-butyl lithium (1.6 M in hexane, 5.6 mL, 9.09 mmol) dropwise over 10 min. The reaction mixture was stirred for 30 min and then a solution of dihydrofuran-3(2H)-one (782 mg, 9.09 mmol) in THF (3 mL) added over 5 min. The reaction mixture was stirred for 1 h at −78° C. then poured into saturated NH4Cl solution. The mixture was extracted with ethyl acetate and the organic layer dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate) to give 3-(3-iodophenyl)tetrahydrofuran-3-ol (2.0 g, 76%) as a colorless liquid: 1H NMR (CDCl3, 300 MHz) δ 7.87 (t, J=1.8 Hz, 1H), 7.64 (td, J=7.8 Hz, 1H), 7.45 (td, J=7.8 Hz, 1H), 7.10 (t, J=8.1 Hz, 1H), 4.26-4.06 (m, 2H), 3.98-3.82 (m, 2H), 2.46-2.32 (m, 1H), 2.30-2.21 (m, 1H).

Provenance & Evidence