Dimethylformamide → HCID 131732177, compound

Temperature

-78 °C

Into a 100-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-(benzyloxy)-5-bromo-1,3-difluorobenzene (7.0 g, 23.40 mmol, 1.00 equiv) in tetrahydrofuran (20 mL) at −78° C. To the resulting mixture was then added n-BuLi (11.3 mL). The resulting mixture was stirred for 1 h at −78° C. To the resulting mixture was then added N,N-dimethylformamide (6 mL). The resulting solution was stirred for 1 h at −78° C. The reaction was then quenched by the addition of water (10 mL). The resulting solution was extracted with ethyl acetate (3×20 mL) and the organic layers combined and dried over anhydrous sodium sulfate. The solids were filtered out and the resulting mixture was then concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:8) to yield 4-(benzyloxy)-3,5-difluorobenzaldehyde/3-(benzyloxy)-2,4-difluorobenzaldehyde as colorless oil.

1. customInto a 100-mL round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. customat −78° C
4. stirringThe resulting solution was stirred for 1 h at −78° C
5. customThe reaction was then quenched by the addition of water (10 mL)
6. extractionThe resulting solution was extracted with ethyl acetate (3×20 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationThe solids were filtered out
9. concentrationthe resulting mixture was then concentrated under vacuum

ORD record

ord-d4b414d8354d4b478613df01385df7df

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08912227B1