[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(Cl)(Cl)(Cl)[Cl:35].CO>CC#N>[Cl:35][CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1
To di(2-pyridinyl)methanol (8.73 g, 46.94 mmol) in CH3CN (100 ml) at 0° C. was added a solution of PPh3 (14.77 gram, 56.32 mmol) in of CCl4 (80 mL) in 1.5 h. The solution was left standing overnight. After addition of MeOH (10 ml) and stirring for 15 min the mixture was concentrated in vacuum to ca 50 ml. To the residue was added of water (100 ml) and the mixture was acidified with 2M HCl to pH=1, and washed twice with 100 ml of CHCl3, the aqueous layer was neutralized with K2CO3 and extracted 4 times with 75 ml of ether. Drying and evaporation of the solvent yielded 2-[chloro(2-pyridinyl)methyl]pyridine (5.41 gram, 56%) as a pale brown solid. Analytically pure material was obtained by column chromatography on silica (ether). 1H-NMR (200 MHz, CDCl3) δ 6.20 (s, 1H), 7.14-7.20 (m, 2H), 7.60-7.73 (m, 4H). 8.51-8.54 (m, 2H). 13C-NMR (50.3 MHz, CDCl3) δ 62.84 (d), 121.3 (d), 121.5 (d), 135.7 (d), 147.7 (d), 156.9 (s). Anal. Cald. for C11H9ClN2: C 64.56, H 4.43, Cl 17.32, N 13.69; Found: C 64.48, H 4.45, Cl 17.29, N 13.49.
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