Sodium Carbonate → 2'-Methoxy-[1,1'-biphenyl]-4-carbaldehyde

HRID 8976

Reaktionsgleichung

Reaktionsgleichung von HRID 8976
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1COCC1.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>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 707414-BromobenzaldehydeHCID 27339582-Methoxyphenylboronic acid

Produkt 1

HCID 27595432'-Methoxy-[1,1'-biphenyl]-4-carbaldehydeAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 22732251Tetrahydrofuran dimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a stirred degassed solution of 4-bromobenzaldehyde (218 mg, 1.18 mmol) and 2-methoxybenzeneboronic acid (188 mg, 1.24 mmol) in DME/THF (5 mL, 4:1) were added a 2 M Na2CO3 solution (1.6 mL) and Pd(PPh3)4 (63 mg, 0.055 mmol). The reaction mixture was flushed with argon and maintained under argon while being heated at 85° C. overnight. The mixture was then cooled and diluted with EtOAc (25 mL) and water (25 mL). The aqueous layer was washed with EtOAc (2×10 mL) and the combined organic extracts dried (Na2SO4), filtered and concentrated. Purification of the resultant oil by column chromatography with silica gel (Hexanes/Et2O, 80:20) afforded the title compound (230 mg, 92%) as a clear oil. 1H NMR (CDCl3) δ 3.84 (s, 3H), 7.01–7.09 (m, 2H), 7.33–7.39 (m, 2H), 7.71 (d, 2H, J=6 Hz), 7.93 (d, 2H, J=6 Hz), 10.05 (s, 1H).

Aufarbeitung

  1. customThe reaction mixture was flushed with argon
  2. temperaturemaintained under argon
  3. temperatureThe mixture was then cooled
  4. additiondiluted with EtOAc (25 mL) and water (25 mL)
  5. washThe aqueous layer was washed with EtOAc (2×10 mL)
  6. dry with materialthe combined organic extracts dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the resultant oil by column chromatography with silica gel (Hexanes/Et2O, 80:20)

Quellen und Nachweise

ORD-Eintrag
ord-6280e45839ed44b288894d446541a1ef
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091217B2

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