Iodoethane → HCID 21650978, compound

Participants

Reaction Conditions

Reaction Steps

A three necked round-bottom flask was purged with argon and then filled with dry THF (250 mL), 1-bromo-3-iodo-benzene (50 g, 176.74 mmol) and ethyl iodide (50 g, 320.57 mmol). The mixture was cooled to −78° C. and LDA (made with 50 mL of iPr2NH and 122.5 mL of BuLi (2.5 M in hexane) in 250 mL of THF) was added slowly at −50° C. The reaction was stirred for 4 hr and poured into sat. aq. NH4Cl solution (1000 mL) and stirred vigorously for 20 min, extracted with DCM. The organic layers were separated, dried over Na2SO4 and evaporated to give the crude product, which was purified by column chromatography to afford 1-bromo-2-ethyl-3-iodo-benzene (D126) (50 g,). δH (CDCl3-d6, 400 MHz): 1.14 (3H, t), 3.06 (2H, q), 6.68 (1H, t), 7.52 (1H, d), 7.70 (1H, d)

Provenance & Evidence