Potassium Carbonate → 4'-Fluorobiphenyl-4-carbaldehyde

HRID 1889676Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1889676
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.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>[F:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 707414-BromobenzaldehydeHCID 2856454-Fluorophenylboronic acid

Produkt 1

HCID 13925504'-Fluorobiphenyl-4-carbaldehydeAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 4-bromobenzaldehyde (1.0 g, 5.4 mmol, 1.0 eq) and 4-fluorophenylboronic acid (0.75 g, 5.4 mmol, 1.0 eq) in toluene was purged with nitrogen for 15 minutes and degassed under vacuum. Dry K2CO3 (1.12 g, 8.12 mmol, 1.5 eq) and tetrakis catalyst (0.3 g, 0.27 mmol, 0.05 eq) were added under nitrogen. The reaction mixture was refluxed under nitrogen for 12 h, quenched with ice water and extracted with ethyl acetate. The organic layer was dried over sodium sulphate and concentrated under vacuum. The residue was purified by silica gel (60-120) column chromatography using 5-10% ethyl acetate/hexane as the eluent to afford the desired compound (0.75 g, 75%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.29-7.35 (t, 2H), 7.77-7.83 (t, 2H), 7.86-7.88 (d, 2H), 7.96-7.98 (d, 2H), 10.03 (s, 1H). MS (ESI): 201.2 (M+H)+.

Aufarbeitung

  1. customdegassed under vacuum
  2. temperatureThe reaction mixture was refluxed under nitrogen for 12 h
  3. customquenched with ice water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by silica gel (60-120) column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1098b388aeb34aa089a00b1fba86cd66
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501992B2

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