Triphenylphosphine → HCID 10947253, compound

A mixture of 705 mg (2.4 mmol) of 2-bromo-4-(trifluoroacetamido)anisole and 625 mg (2.4 mmol) of triphenylphosphine in 25 mL of CC14 was heated at reflux. After 4 h, a second 625 mg portion of triphenylphosphine was added and heating was continued for 16 h. The reaction mixture was cooled and concentrated in vacuo. The residue was dissolved in 15 mL of DMF, treated with 650 mg (10.0 mmol) of NaN3 and stirred at rt. After 1.5 h, the reaction mixture was concentrated in vacuo and the residue was partitioned between 200 mL of ether and 100 mL of H2O. The layers were separated; the organic layer was washed with 2×100 mL of H2O, dried over MgSO4 and concentrated in vacuo. Flash chromatography on 40 g of silica gel using 4:1 v/v hexanes/ether as the eluant afforded 700 mg (91%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ 4.01 (s, 3H), 7.07 (d, J=8.5, 1H), 7.43 (dd, J=8.5, 2.5), 7.71 (d, J=2.5, 1H).

1. temperaturewas heated
2. temperatureat reflux
3. temperatureheating
4. waitwas continued for 16 h
5. temperatureThe reaction mixture was cooled
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in 15 mL of DMF
8. waitAfter 1.5 h
9. concentrationthe reaction mixture was concentrated in vacuo
10. customthe residue was partitioned between 200 mL of ether and 100 mL of H2O
11. customThe layers were separated
12. washthe organic layer was washed with 2×100 mL of H2O
13. dry with materialdried over MgSO4
14. concentrationconcentrated in vacuo

ORD record

ord-d28ad65a31ae43719b04bbf3ae43d75b

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05929094