Dichloromethane → 3-(2,3'-Diisobutyl-4'-methoxy-biphenyl-4-yl)propionitrile

HRID 25844

Reaktionsgleichung

Reaktionsgleichung von HRID 25844
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]#[N:16])=[CH:9][C:8]=1[CH2:17][CH:18]([CH3:20])[CH3:19])(=O)=O.[CH2:23]([C:27]1[CH:28]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[CH:24]([CH3:26])[CH3:25].C([O-])([O-])=O.[Na+].[Na+].C(Cl)Cl>COCCOC.CCO.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>[CH2:17]([C:8]1[CH:9]=[C:10]([CH2:13][CH2:14][C:15]#[N:16])[CH:11]=[CH:12][C:7]=1[C:29]1[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:27]([CH2:23][CH:24]([CH3:26])[CH3:25])[CH:28]=1)[CH:18]([CH3:20])[CH3:19]

Komponenten

7

Edukt 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 121347033-Isobutyl-4-(trifluoromethylsulfonyloxy)benzenepropanenitrileHCID 121347052-(3-Isobutyl-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 225652533-(2,3'-Diisobutyl-4'-methoxy-biphenyl-4-yl)propionitrileAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 20074477Dimethoxyethane ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

294.8 mg (0.88 mmol) 4-(2-Cyanoethyl)-2-isobutylphenyl-trifluormethanesulfonate (6), 312.9 mg (1.08 mmol, 1.23 eq.) 2-(3-Isobutyl-4-methoxyphenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (11) and 156 mg (135 μmol, 0.15 eq.) Pd(Ph3P)4 were dissolved in 20 ml DME/EtOH (9+1). To this yellow solution 0.88 ml (1.76 mmol, 2.00 eq.) of a 2 M aq. Na2CO3-solution was added and the resulting mixture was heated at 80° C. for 17 h. After concentrating the mixture in vacuo the residue was taken up in water and extracted with CH2Cl2. The comb. org. fractions were dried over MgSO4 and evaporated. Column chromatography (CH2Cl2) yielded 305.9 mg (0.88 mmol, 99.45%) 3-(2,3′-Diisobutyl-4′-methoxy-biphenyl-4-yl)propionitrile (73) as a clear oil. Rf (CH2Cl2)=0.68. 1H-NMR (500 MHz, CDCl3): δ=0.67 (d, 6H, J=6.62 Hz, 2*CH3), 0.85 (d, 6H, J=6.62 Hz, 2*CH3), 1.61 (m, 1H, CH), 1.89 (m, 1H, CH), 2.44 (d, 2H, J=7.25 Hz, CH2), 2.45 (d, 2H, J=7.25 Hz, CH2), 2.59 (t, 2H, J=7.41 Hz, CH2CH2CN), 2.91 (t, 2H, J=7.41 Hz, CH2CH2CN), 3.79 (s, 3H, OCH3), 6.80 (d, 1H, J=8.36 Hz), 6.94 (d, 1H, J=2.21 Hz), 6.98-7.04 (m, 3H), 7.09 (d, 1H, J=7.57 Hz). MS (EI): m/z=350 (23), 349 (90), 307 (10), 306 (35), 290 (39), 250 (15), 248 (17), 247 (100), 246 (24), 209 (21), 191 (16), 178 (10), 147 (10), 145 (17), 144 (19), 117 (13), 105 (25), 83 (11), 57 (18). HR-MS (EI): Calcd. for C24H31NO: 349.240564. Found: 349.240765.

Aufarbeitung

  1. concentrationAfter concentrating the mixture in vacuo the residue
  2. extractionextracted with CH2Cl2
  3. dry with materialfractions were dried over MgSO4
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d956c5d8dd904c77b91edd467b105a47
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858600B2

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