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Sodium Carbonate → HCID 69870925, Verbindung

HRID 2417099
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2417099
[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1Br)([CH3:7])[CH3:6])[CH3:2].[C:25]1(B(O)O)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(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>[CH2:1]([O:3][C:4](=[O:24])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][C:10]=1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:7])[CH3:6])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 69871067HCID 69871067, Verbindung

Produkt 1

HCID 69870925HCID 69870925, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 702
Ethanol
Lösungsmittel
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

2-(4-Benzyloxy-2-bromo-phenoxy)-2-methyl-propionic acid ethyl ester (3.00 g, 7.63 mmol) and phenyl boronic acid (1.12 g, 9.15 mmol) were dissolved in toluene (75 mL)/ethanol (75 mL). The solution was degassed (2×), and tetrakis(triphenylphosphine)palladium (70 mg, 0.061 mmol) was added followed by aqueous 2M Na2CO3 solution (7.63 mL, 15.3 mmol). The reaction mixture was degassed (2×) and heated to reflux under argon for 16 h. The reaction mixture cooled and partitioned between ethyl acetate (200 mL) and H2O (75 mL). The organic layer was washed with brine (75 mL), dried (Na2SO4), and concentrated to a light brown oil (3.58 g). The crude product was used directly in the next reaction: 1H NMR (400 MHz, CDCl3) δ 1.266 (t, 3H, J=7.1 Hz), 1.273 (s, 6H), 4.20 (q, 2H, J=7.1 Hz), 5.03 (s, 2H), 6.82 (dd, 1H, J=3.2, 9.0 Hz), 6.92 (d, 1H, J=8.8 Hz), 6.97 (d, 1H, J=3.0 Hz), 7.28-7.44 (m, 8H), 7.51-7.60 (m, 2H); MS (ES) m/e # [M+1].

Aufarbeitung

  1. additionwas added
  2. customThe reaction mixture was degassed (2×)
  3. temperatureheated
  4. temperatureto reflux under argon for 16 h
  5. temperatureThe reaction mixture cooled
  6. custompartitioned between ethyl acetate (200 mL) and H2O (75 mL)
  7. washThe organic layer was washed with brine (75 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated to a light brown oil (3.58 g)
  10. customThe crude product was used directly in the next reaction

Quellen und Nachweise

ORD-Eintrag
ord-9358bdbe50a749f39e3a23d2a95516c2
Quelldatensatz
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06825222B2

Notizen zur Reaktion

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