Water → 4'-(Benzyloxy)-4-fluoro-2',6'-dimethylbiphenyl-3-carbaldehyde

HRID 2280669Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2280669
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12](B(O)O)=[C:11]([CH3:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]1[CH:28]=[CH:27][C:26](Br)=[CH:25][C:22]=1[CH:23]=[O:24].C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:26]2[CH:27]=[CH:28][C:21]([F:20])=[C:22]([CH:23]=[O:24])[CH:25]=2)=[C:11]([CH3:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

9

Edukt 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 23157199(4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid

Produkt 1

HCID 897017664'-(Benzyloxy)-4-fluoro-2',6'-dimethylbiphenyl-3-carbaldehydeAusbeute 116,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylKatalysatorHCID 1140TolueneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid 12b (256 mg, 1 mmol), 2-fluoro-5-bromo-benzaldehyde (203 mg, 1 mmol), 2M aqueous sodium carbonate solution (1 mL, 2 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (37 mg, 0.08 mmol) and tris(dibenzylideneacetone)dipalladium (18 mg, 0.02 mmol) were dissolved in 3 mL of a mixture of the solvents ethylene glycol dimethyl ether and toluene (V/V=1:2). The reaction mixture was heated at 100° C. for 2 hours, and then at 120° C. for 0.5 hours under microwave conditions. The resulting mixture was mixed with 10 mL of water and extracted with ethyl acetate (10 mL×3). The combined organic extracts were washed with saturated sodium chloride solution (30 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with elution system B to obtain the title compound 4′-(benzyloxy)-4-fluoro-2′,6′-dimethylbiphenyl-3-carbaldehyde 18a (390 mg, yield 58.4%) as a colorless slime.

Aufarbeitung

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
  3. dry with materialdried with anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography with elution system B

Quellen und Nachweise

ORD-Eintrag
ord-4a878c20b66b4bb5ae5a86355ec40e88
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09139548B2

Notizen zur Reaktion

Wird geladen…