[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Br:10])[C:3]=1[CH2:11][C:12]#[N:13].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C(=O)(O)[O-].[Na+].[Cl-].[Na+]>C(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][O:14]2)[CH:5]=[C:4]([Br:10])[C:3]=1[CH2:11][C:12]#[N:13]
A solution of 2,6-dibromo-4-hydroxymethyl-phenyl)-acetonitrile (59) (1.4 g, 4.59 mmol) in methylene chloride (30 mL) at room temperature was treated with 3,4-dihydro-2H-pyran (0.46 mL, 5.04 mmol) and p-toluenesulfonic acid monohydrate (16.10 mg, 0.085 mmol). The reaction mixture was stirred for 45 min and was then treated with a saturated aqueous sodium bicarbonate solution (3 mL), a saturated aqueous sodium chloride solution (10 mL) and water (10 mL). This mixture was extracted with methylene chloride (3×50 mL). The organic layers were combined and washed with a saturated aqueous sodium chloride solution (30 mL), dried with magnesium sulfate, filtered and concentrated under vacuum. The resulting oil was purified by flash chromatography (Isco 120 g column) using silica gel eluted with 15% ethyl acetate in hexanes. The desired fractions were collected and concentrated under vacuum to afford an oil which was dried under high vacuum to afford of [2,6-dibromo-4-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-acetonitrile (60) as a pale yellow oil (1.52 g, 85.4%). Used without further purification. Molecular Weight=389.0892; Exact Mass=386.9470
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