Allyltributylstannane → Benzene, 4-nitro-1-(2-propen-1-yl)-2-(trifluoromethyl)-

HRID 1466120

Reaktionsgleichung

Reaktionsgleichung von HRID 1466120
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH2:15]([Sn](CCCC)(CCCC)CCCC)[CH:16]=[CH2:17].[Cl-].[Li+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH2:17][CH:16]=[CH2:15])=[C:3]([C:11]([F:14])([F:13])[F:12])[CH:4]=1)([O-:10])=[O:9]

Komponenten

7

Edukt 3

HCID 90628AllyltributylstannaneHCID 1361982-Bromo-5-nitrobenzotrifluorideHCID 433294Lithium Chloride

Produkt 1

HCID 9816036Benzene, 4-nitro-1-(2-propen-1-yl)-2-(trifluoromethyl)-

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of 1-bromo-4-nitro-2-(trifluoromethyl)benzene (1.0 g, 3.7 mmol), Allyl Tri-n-butyltin (1.4 mL, 4.4 mmol), Lithium Chloride (470 mg, 11 mmol), and Palladium Tetrakis (210 mg, 0.18 mmol) in toluene (30 mL) was heated to reflux for 16 hours under nitrogen. TLC showed complete reaction at that point. The reaction was diluted with ethyl acetate, adsorbed onto silica gel, and purified by silica gel chromatography to afford the title product.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours under nitrogen
  3. customreaction at that point
  4. custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7f88ea31ffa94c30b451d58c8701fb8c
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999990B2

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