4-Fluorophenol → HCID 9913245, compound

Participants

Reaction Steps

Diisopropyl azodicarboxylate (57 mg, 0.27 mmol) was added dropwise to a stirred solution of the alcohol from Step 5 (75 mg, 0.19 mmol), PPh3 (75 mg, 0.27 mmol) and 4-fluorophenol (26 mg, 0.23 mmol) in THF (10 mL) under N2 and the resulting mixture was stirred at RT for 2 hours. Further DIAD (19 mg, 0.09 mmol), PPh3 (25 mg, 0.09 mmol) and 4-fluorophenol (11 mg, 0.09 mmol) were added and stirring was continued for a further 30 min. The reaction mixture was then concentrated under reduced pressure while loading on to MgSO4 and then purified by column chromatography on silica eluting with 100% Et2O to yield the desired ether (19 mg, 20%). 1H NMR (CDCl3, 360 MHz) δ 7.58-7.53 (2H, s), 7.49 (1H, t, J=7.5 Hz), 7.37 (1H, d, J=7.5 Hz), 6.97 (4H, app. d, J=6.1 Hz), 6.41 (1H, s), 5.05 (2H, s), 4.99 (1H, s), 3.88 (3H, s), 3.48 (2H, q, J=8.9 Hz), 1.81 (6H, s). MS (ES+) C22H23F4N3O3S requires: 485, found: 486 (M+H+, 100%).

Provenance & Evidence