Toluene → Ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3,4-dimethylnaphthalen-2-yl)acetate

HRID 514123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 514123
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:3]=1[CH3:30].[CH3:31]B1OB(C)OB(C)O1.C([O-])([O-])=O.[K+].[K+].C1(C)C=CC=CC=1>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CCO>[C:26]([O:25][CH:19]([C:4]1[C:3]([CH3:30])=[C:2]([CH3:31])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21])([CH3:28])([CH3:27])[CH3:29]

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 67126305Ethyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

Produkt 1

HCID 67126302Ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3,4-dimethylnaphthalen-2-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A suspension of ethyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate (25 mg, 51 μmol), trimethylboroxine (21 μL, 0.153 mmol), PdCl2(dppf) (3.7 mg, 5.1 μmol), K2CO3 (70 mg, 0.510 mmol), PhMe (500 μL), EtOH (absolute, 250 μL), and H2O (250 μL) was stirred in a sealed vessel at 100° C. for 3 h. The reaction was cooled to 23° C., diluted with H2O and extracted with EtOAc (3×). Combined organic phases were dried (Na2SO4), filtered, and concentrated, giving crude product. (Yield was not found). 1H NMR (400 MHz, CD3OD) δ 8.08 (d, J=8.2 Hz, 1H), 7.48-7.44 (m, 3H), 7.29-7.26 (m, 4H), 5.15 (s, 1H), 4.20-4.12 (m, 2H), 2.65 (s, 3H), 2.55 (s, 3H), 1.21 (t, J=7 Hz, 3H), 1.00 (s, 9H).

Aufarbeitung

  1. temperatureThe reaction was cooled to 23° C.
  2. extractionextracted with EtOAc (3×)
  3. dry with materialCombined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customgiving crude product
  7. custom(Yield

Quellen und Nachweise

ORD-Eintrag
ord-eb50a7aa1d1e4756b1f980f0a877f447
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102614B2

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