Triphenylphosphine → HCID 18796385, compound

3-Bromo-4-(trifluoroacetamido)anisole (4.7 g, 0.16 mol) was suspended in carbon tetrachloride (60 ml) and triphenylphosphine (6.2 g, 0.024 mol) was added. The reaction was heated at reflux for 12 hours. The reaction was allowed to cool to ambient temperature, and filtered. The solid was washed thoroughly with ethyl acetate:diethyl ether (1:1, 200 ml:200 ml). The filtrate was concentrated in vacuo to afford a red solid. This solid was dissolved in N,N-dimethylformamide (10 ml) and this solution was added to sodium azide (1.55 g, 0.024 mol). The reaction was stirred at ambient temperature for 12 hours, and diluted with water (100 ml). The product was extracted into ethyl acetate (3×50 ml) and the combined organics were washed with brine (100 ml), dried over magnesium sulphate and the solvent removed in vacuo. Chromatography on silica eluting with 10% ethyl acetate in hexane afforded the title compound as a pale orange solid (4.2 g, 66%), m/z (ES+) 323 (M+ +H, 100%). 1H NMR (250 MHz, CDCl3) δ 3.92 (3H, s), 7.03 (1H, dd J 2.7 Hz, J 8.8 Hz), 7.30 (1H, d, J 2.7 Hz), 7.34 (1H, d, J 8.8 Hz).

1. temperatureThe reaction was heated
2. temperatureat reflux for 12 hours
3. filtrationfiltered
4. washThe solid was washed thoroughly with ethyl acetate:diethyl ether (1:1, 200 ml:200 ml)
5. concentrationThe filtrate was concentrated in vacuo
6. customto afford a red solid
7. extractionThe product was extracted into ethyl acetate (3×50 ml)
8. washthe combined organics were washed with brine (100 ml)
9. dry with materialdried over magnesium sulphate
10. customthe solvent removed in vacuo

ORD record

ord-a8176652e8e24dcc9bdb52df7eca17a3

Source dataset

uspto-grants-2000_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06046195