Tetrahydrofuran → 1-Bromo-4-(ethenyloxy)benzene

To a THF (250 mL) solution of 1-bromo-4-(2-chloroethoxy)benzene (58.6 g, 249 mmol) prepared in Example 5 (5a) was added tert-butoxy potassium (33.7 g, 300 mmol) at −10° C. over 10 minutes. The resulting mixture was stirred at room temperature for 21 hours. Water (500 mL) was added thereto, and the mixture was extracted with methyl tert-butyl ether (200 mL, 150 mL) twice. The organic layers were combined, washed with saturated brine (100 mL) twice, and dried over anhydrous magnesium sulfate. Then, the solvent was evaporated. The resulting residue was dissolved in n-hexane (100 mL), and the precipitated insoluble substance was removed by filtration, and this insoluble substance was further washed with n-hexane (5 mL) five times. These filtrates were combined and concentrated, and then purified by silica gel column chromatography (n-hexane) to give 39.0 g of the title compound (colorless oil, yield: 79%).

1. extractionthe mixture was extracted with methyl tert-butyl ether (200 mL, 150 mL) twice
2. washwashed with saturated brine (100 mL) twice
3. dry with materialdried over anhydrous magnesium sulfate
4. customThen, the solvent was evaporated
5. dissolutionThe resulting residue was dissolved in n-hexane (100 mL)
6. customthe precipitated insoluble substance was removed by filtration
7. washthis insoluble substance was further washed with n-hexane (5 mL) five times
8. concentrationconcentrated
9. custompurified by silica gel column chromatography (n-hexane)

ORD record

ord-063d0935fb7047478ca58defb71c4f47

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08344029B2