Dimethylformamide → HCID 86622730, compound

Temperature

-20 °C

To a solution of 1-fluoro-3-isobutoxybenzene (1.7 g, 10 mmol, EXAMPLE 16, Step 1) in tetrahydrofuran (15 mL) was added dropwise s-BuLi (0.99 M in cyclohexane, 12 mL, 12 mmol) at −78° C. under nitrogen atmosphere, and the mixture was stirred for 1 h. N,N-dimethylformamide (1.2 mL, 15 mmol) was added to the mixture, and the mixture was warm to −20° C. After being stirred at −20° C. for 1 h, the mixture was quenched with aq. sodium hydrogencarbonate (30 mL). The mixture was extracted with ethyl acetate (60 mL) and washed with water (30 mL). The extract was dried over magnesium sulfate and concentrated in vacuo to give an oil. The residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 30:1) to give 1.2 g (61%) of the title compound as a colorless oil.

1. stirringAfter being stirred at −20° C. for 1 h
2. customthe mixture was quenched with aq. sodium hydrogencarbonate (30 mL)
3. extractionThe mixture was extracted with ethyl acetate (60 mL)
4. washwashed with water (30 mL)
5. dry with materialThe extract was dried over magnesium sulfate
6. concentrationconcentrated in vacuo
7. customto give an oil
8. customThe residual oil was purified by silica gel column chromatography (hexane/ethyl acetate 30:1)

ORD record

ord-40083fa9a0b94013830e6af23c0a971b

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08816090B2