Allyl bromide → 1-(Allyloxy)-3,5-difluoro-2-nitrobenzene

A solution of 3,5-difluoro-2-nitrophenol and 3,5-difluoro-4-nitrophenol (3.54 g, 20 mmol), allyl bromide (2.9 g, 24 mmol) and potassium carbonate (8.3 g, 60 mmol) in acetone (50 mL) was refluxed for 2 h. The progress of reaction was monitored by TLC. After completion, the reaction mixture was concentrated under reduced pressure at 25° C. The residue was diluted with water extracted with ether. The organic layer was washed with water, dried over anhydrous Na2SO4 and concentrated under reduced pressure at 25° C. The residue obtained was purified by silica gel column chromatography (0-1% ethyl acetate-hexane) to yield 1-(allyloxy)-3,5-difluoro-2-nitrobenzene (934 mg). 1H-NMR (400 MHz, CD3OD): δ 4.72 (2H, d), 5.32 (1H, d J=10.8), 5.42 (1H, d, J=17.2), 5.98-6.02 (1H, m), 6.85 (1H, dt), 6.96 (1H, d).

1. customThe progress of reaction
2. concentrationAfter completion, the reaction mixture was concentrated under reduced pressure at 25° C
3. additionThe residue was diluted with water
4. extractionextracted with ether
5. washThe organic layer was washed with water
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated under reduced pressure at 25° C
8. customThe residue obtained
9. customwas purified by silica gel column chromatography (0-1% ethyl acetate-hexane)

ORD record

ord-803b505211514cf285cb88de3791d2c1

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034861B2