Sodium Chloride → [2,6-Dibromo-4-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-acetonitrile

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

1. extractionThis mixture was extracted with methylene chloride (3×50 mL)
2. washwashed with a saturated aqueous sodium chloride solution (30 mL)
3. dry with materialdried with magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated under vacuum
6. customThe resulting oil was purified by flash chromatography (Isco 120 g column)
7. washeluted with 15% ethyl acetate in hexanes
8. customThe desired fractions were collected
9. concentrationconcentrated under vacuum
10. customto afford an oil which
11. customwas dried under high vacuum

ORD record

ord-3167aac71b6b483d94b0756a6caffe80

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

USRE046024E1