[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4]Br.[C:10]([C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=1[OH:19])#[N:11].[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][O:19][C:13]1[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=1[C:10]#[N:11]To a stirred mixture of 2-bromo-benzyl bromide (5.00 g, 20.0 mmol) and 2-cyano-4-chloro-phenol (13.2 g, 21.0 mmol) in anhydrous DMF under argon was added 95% NaH (0.56 g, 22.0 mmol) portionwise. This reaction mixture was stirred at room temperature for 1.5 hours and then quenched with water. The resulting mixture was diluted with ether (400 mL), and washed sequentially with water (3×100 mL), 1N NaOH solution (2×30 mL), saturated NaHCO3 solution (1×60 mL) and brine (1×60 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give 5.30 g of 2-(2-Bromo-benzyloxy)-5-chloro-benzonitrile Example 348A in 82% yield. HPLC Rt=3.89 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm) LC/MS: M+H=322
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