Water → 2-[2-(3-Fluorophenyl)vinyl]naphthalene

Temperature

-30 °C

In the step, 35.00 g (77.55 mmol) of (3-fluorobenzyl)triphenylphosphonium bromide was suspended in 150 ml of THF, and the suspension was cooled to −30° C. and added with 10.25 g (=88.61 mmols) of potassium t-butoxide under stirring. After the addition was finished, the reaction solution was stirred at the same temperature for 1 hour, a 50 ml THF solution of 8.65 g (=55.38 mmol) of 2-naphthoaldehyde was dropped into the same, and then the mixture was slowly heated to room temperature. After being stirred for 18 hours, the reaction mixture was added into iced water, and the mixture was extracted thrice with toluene. The extract was washed thrice with water and then dried with anhydrous MgSO4. After the solvent was evaporated under a reduced pressure, the obtained yellow solid of 43.34 g was purified with silica gel chromatography using heptane as the eluent to obtain 11.54 g of 2-[2-(3-fluorophenyl)vinyl]naphthalene as a white solid.

1. additionAfter the addition
2. stirringthe reaction solution was stirred at the same temperature for 1 hour
3. temperaturewas slowly heated to room temperature
4. stirringAfter being stirred for 18 hours
5. extractionthe mixture was extracted thrice with toluene
6. washThe extract was washed thrice with water
7. dry with materialdried with anhydrous MgSO4
8. customAfter the solvent was evaporated under a reduced pressure
9. customthe obtained yellow solid of 43.34 g was purified with silica gel chromatography

ORD record

ord-10091da3b55442d5ac5741199cfbd856

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790915B2