Iodoethane → HCID 21650978, compound

Temperature

-78 °C

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)

1. customA three necked round-bottom flask was purged with argon
2. stirringstirred vigorously for 20 min
3. extractionextracted with DCM
4. customThe organic layers were separated
5. dry with materialdried over Na2SO4
6. customevaporated
7. customto give the crude product, which
8. customwas purified by column chromatography

ORD record

ord-23def6e6ce044eb9b1ec496c969d62bf

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389508B2