4,4,5,5-Tetramethyl[1,3,2]dioxaborolane → 2-(2-(Butyloxy)-5-(methyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 2101748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2101748
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[O:10][CH2:11][CH2:12][CH2:13][CH3:14].O(C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:54][C:55]1([CH3:62])[C:59]([CH3:61])([CH3:60])[O:58][BH:57][O:56]1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:11]([O:10][C:3]1[CH:4]=[CH:5][C:6]([O:8][CH3:9])=[CH:7][C:2]=1[B:57]1[O:58][C:59]([CH3:61])([CH3:60])[C:55]([CH3:62])([CH3:54])[O:56]1)[CH2:12][CH2:13][CH3:14]

Komponenten

6

Edukt 3

HCID 27347684,4,5,5-Tetramethyl[1,3,2]dioxaborolaneHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 578018162-Bromo-1-butoxy-4-methoxybenzene

Produkt 1

HCID 576724442-(2-(Butyloxy)-5-(methyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

A mixture of 2-bromo-1-butoxy-4-methoxybenzene (1.2 g, 4.7 mmol), TEA (2.6 mL, 19 mmol), (oxydi-2,1-phenylene)bis(diphenylphosphine) (0.51 g, 0.95 mmol) (Aldrich, CAS# 166330-10-5), palladium(II) acetate (0.11 g, 0.47 mmol), and 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.1 mL, 14 mmol) (Aldrich, CAS# 25015-63-8) in 1,4-dioxane (5.0 mL) was stirred overnight at 95° C. The mixture was cooled to room temperature, quenched with saturated aqueous ammonium chloride, and extracted with ether. The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford compound C.3 (0.60 g, 41% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.16 (d, J=3.1 Hz, 1H), 6.91 (dd, J=3.1, 9.0 Hz, 1H), 6.79 (d, J=9.0 Hz, 1H), 3.91 (t, J=6.3 Hz, 2H), 3.78 (s, 3H), 1.75 (m, 2H), 1.54 (m, 2H), 1.34 (s, 12H), 0.96 (t, J=7.4, 3H).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with saturated aqueous ammonium chloride
  3. extractionextracted with ether
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel flash chromatography (0-10% EtOAc/hexane)
  7. customto afford compound C.3 (0.60 g, 41% yield) as a colorless oil

Quellen und Nachweise

ORD-Eintrag
ord-e64b106892d4477aba7d7786c397c676
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572934B2

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