Allyl bromide → HCID 14085931, compound

Temperature

50 °C

To a solution of 4-(trifluoromethyl)phenol (50 g, 308 mmol) in CH3CN (600 ml) was added potassium carbonate (64 g, 463 mmol, 1.5 eq) and allyl bromide (48 g, 397 mmol, 1.3 eq) with stirring for overnight at 50° C. in an oil bath. The solids were filtered off and the filtrate was concentrated to a minimum volume, which was diluted by water (200 ml) and extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine (2×200 ml), dried over anhydrous magnesium sulfate, filtered, and then concentrated under vacuum to afford 1-(prop-2-en-1-yloxy)-4-(trifluoromethyl)benzene as yellow oil (35 g, 56%); 1H NMR (300 MHz, CDCl3): δ 7.52 (d, J=8.7 Hz, 2H), 6.96 (d, J=8.7 Hz, 2H), 5.98-6.11 (m, 1H), 5.30-5.46 (m, 2H), 4.57-4.58 (m, 2H).

1. filtrationThe solids were filtered off
2. concentrationthe filtrate was concentrated to a minimum volume, which
3. additionwas diluted by water (200 ml)
4. extractionextracted with ethyl acetate (3×100 ml)
5. washThe combined organic layers were washed with brine (2×200 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated under vacuum

ORD record

ord-31eb37fcb4da4ffb81e1789ebc950278

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249102B2