Iodine → HCID 90418293, compound

Temperature

-78 °C

Into a 25-mL round-bottom flask (1 atm) purged and maintained with an inert atmosphere of nitrogen, was placed (i-Pr)2NH (1.26 g, 12.48 mmol, 1.25 equiv), tetrahydrofuran (7 mL). This was followed by the addition of n-BuLi (2.5M in hexane) (4.8 mL) dropwise with stirring at −78° C. The mixture was stirred for 1 h at −78° C. Then this solution was added to the solution a solution of 1-bromo-2-fluoro-4-methoxybenzene (2.04 g, 9.95 mmol, 1.00 equiv) in tetrahydrofuran (5 mL) at −78 degree C. and stirred for 30 min, then I2 (3.048 g, 12.00 mmol, 1.2 equiv) was added. The resulting solution was stirred for 30 min at −78° C. in a liquid nitrogen bath. The reaction progress was monitored by GCMS. The reaction was then quenched by the addition of 10 mL of water. The resulting solution was extracted with 2×20 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with petroleum ether. This resulted in 2.0 g (61%) of 1-bromo-2-fluoro-3-iodo-4-methoxybenzene as a light yellow solid. Mass spectrum (GC, m/z): Calcd. for C7H5BrFIO, 330.9 (M). found 330.9.

1. customInto a 25-mL round-bottom flask (1 atm) purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringThe mixture was stirred for 1 h at −78° C
4. stirringand stirred for 30 min
5. stirringThe resulting solution was stirred for 30 min at −78° C. in a liquid nitrogen bath
6. customThe reaction was then quenched by the addition of 10 mL of water
7. extractionThe resulting solution was extracted with 2×20 mL of ethyl acetate
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated under vacuum
10. customThis resulted in 2.0 g (61%) of 1-bromo-2-fluoro-3-iodo-4-methoxybenzene as a light yellow solid

ORD record

ord-fd5709c1e04649699fafdb9bd071cc6e

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067898B1