Chloride → 2-(4-Fluorophenylmethyl)indene

HRID 11967

Reaktionsgleichung

Reaktionsgleichung von HRID 11967
[Mg].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Cl)=[CH:5][CH:4]=1.[Cl-].Br[C:13]1[CH2:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:13]2[CH2:21][C:20]3[C:15]([CH:14]=2)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 312ChlorideHCID 96024-Fluorobenzyl chlorideHCID 5755861H-Indene, 2-bromo-HCID 5462224Magnesium

Produkt 1

HCID 219769972-(4-Fluorophenylmethyl)indene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418745HCID 178418745, VerbindungKatalysatorHCID 3283Diethyl EtherLösungsmittel3×

Versuchsvorschrift

To a suspension of freshly ground magnesium (0.58 g, 23 mmol) in 100 mL of ether was added about 3 mL of a 15 mL ether solution containing 3.0 g (21 mmol) of 4-fluorophenylmethyl chloride. The system was carefully heated and after initiation of the reaction, the remaining chloride solution added over 30 minutes while maintain a gentle reflux. After refluxing for 1.5 hours, the Grignard solution was cooled and cannulated to a mixture of 3.65 g (19 mmol) of 2-bromo-indene, 150 mg (0.20 mmol) of NiCl2(dppp) and 100 mL of ether. The system was gently heated to reflux overnight and then cooled and quenched by adding 150 mL of 1.0 M aqueous hydrochloric acid. The product was isolated and purified (hexanes/silica) as for 2-benzyl-indene. Yield: 3.45 g, 74 percent

Aufarbeitung

  1. temperatureThe system was carefully heated
  2. customafter initiation of the reaction
  3. temperaturewhile maintain a gentle reflux
  4. temperatureAfter refluxing for 1.5 hours
  5. temperaturethe Grignard solution was cooled
  6. temperatureThe system was gently heated
  7. temperatureto reflux overnight
  8. temperaturecooled
  9. customquenched
  10. additionby adding 150 mL of 1.0 M aqueous hydrochloric acid
  11. customThe product was isolated
  12. custompurified (hexanes/silica) as for 2-benzyl-indene

Quellen und Nachweise

ORD-Eintrag
ord-c95ea336c63e4d4ea8961bed6584d030
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098356B2

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