Water → 2-{3-Fluoro-4-[2-(4-fluorophenyl)vinyl]phenyl}naphthalene

HRID 1712198

Reaktionsgleichung

Reaktionsgleichung von HRID 1712198
[Br-].[F:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.CC(C)([O-])C.[K+].[F:35][C:36]1[CH:43]=[C:42]([C:44]2[CH:53]=[CH:52][C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH:45]=2)[CH:41]=[CH:40][C:37]=1[CH:38]=O.O>C1COCC1>[F:35][C:36]1[CH:43]=[C:42]([C:44]2[CH:53]=[CH:52][C:51]3[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=3)[CH:45]=2)[CH:41]=[CH:40][C:37]=1[CH:38]=[CH:7][C:6]1[CH:5]=[CH:4][C:3]([F:2])=[CH:28][CH:27]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10837295(4-Fluorobenzyl)triphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 549124512-Fluoro-4-(naphthalen-2-yl)benzaldehyde

Produkt 1

HCID 686152802-{3-Fluoro-4-[2-(4-fluorophenyl)vinyl]phenyl}naphthaleneAusbeute 83,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

In the step, 6.30 g (15.48 mmol) of (4-fluorobenzyl)triphenylphosphonium bromide was suspended in 50 ml of THF, and the suspension was cooled to −30° C. and added with 1.74 g (=15.48 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 25 ml THF solution of 3.00 g (11.99 mmol) of 2-fluoro-4-naphthalene-2-yl-benzaldehyde 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 12.73 g was purified with silica gel chromatography using heptane as the eluent to obtain 3.44 g of 2-{3-fluoro-4-[2-(4-fluorophenyl)vinyl]phenyl}naphthalene as a white solid.

Aufarbeitung

  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 12.73 g was purified with silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4d7a06a2951e4ae7b449caffef22319b
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790915B2

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