C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[Cl:31])=[N+]=[N-].N#N.CO>C1COCC1.O>[Cl:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[CH2:23][NH2:20]Add triphenylphosphine (129.9 g, 495 mmol) to a solution of 1-azidomethyl-2-chloro-4-fluoro-benzene (61.2 g, 330 mmol) in THF (500 mL) and water (30 mL). Stir at RT until no more N2 is evolved. Add 100 mL MeOH and stir at RT overnight. Concentrate; acidify to pH 1 with 1N HCl solution, wash with CH2Cl2 (3 times). Basify aqueous layer with 5N NaOH solution, extract with CH2Cl2 (3 times), dry over MgSO4. Concentrate to afford the title compound (38.5 g, 73%) as a clear liquid. MS(IS) 160 (M+1). 1H NMR (400 MHz, CDCl3): 3.90 (s, 2H); 6.96 (t, 1H, J=6.4 Hz); 7.11 (d, 1H, J=8.3 Hz); 7.36 (t, 1H, J=6.4 Hz).
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