Ethyl Acetate → Tert-butyl 4'-(benzyloxy)-2'-nitrobiphenyl-4-ylcarbamate

HRID 1879530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1879530
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Cl)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:27]2[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:29][CH:28]=2)O1.C([O-])([O-])=O.[Na+].[Na+].CCOC(C)=O>O1CCOCC1.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>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:27]2[CH:28]=[CH:29][C:30]([NH:33][C:34](=[O:40])[O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[CH:31][CH:32]=2)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2734617tert-butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamateHCID 110436225-Benzyloxy-2-chloro-nitrobenzene

Produkt 1

HCID 58160246Tert-butyl 4'-(benzyloxy)-2'-nitrobiphenyl-4-ylcarbamateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To 4-(benzyloxy)-1-chloro-2-nitrobenzene (526 mg, 2 mmol) and tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (670 mg, 2.1 mmol) in 12 mL dioxane was added 4 mL of a 1 M Na2CO3 (aq) solution and Tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol). The suspension was heated at reflux for 15 h under Ar atmosphere and cooled to rt. It was added EtOAc (100 mL) and washed with brine (80 mL), water (80 mL), and dried over MgSO4. After solvent removal, the residue was chromatographed (hexane/EtOAc) to afford tert-butyl 4′-(benzyloxy)-2′-nitrobiphenyl-4-ylcarbamate as a yellow solid (740 mg, 88%). 1H NMR (400 MHz, CDCl3) δ 7.44-7.34 (m, 8H), (d, J=8.4 Hz, 1H), 7.20-7.16 (m, 3H), 6.50 (s, 1H), 5.12 (s, 2H), 1.51 (s, 9H); MS (ESI) m/z 443 (M+Na+).

Aufarbeitung

  1. temperatureThe suspension was heated
  2. temperatureat reflux for 15 h under Ar atmosphere
  3. washwashed with brine (80 mL), water (80 mL)
  4. dry with materialdried over MgSO4
  5. customAfter solvent removal
  6. customthe residue was chromatographed (hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-4481982c35d04724826a0e195738e877
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318132B2

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