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Nitrogen → 2',3',4'-Trimethoxy-biphenyl-3-carboxylic acid methyl ester

HRID 1944252
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1944252
N#N.[CH3:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[CH:7][C:6]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].[CH3:24][O:25][C:26](=[O:34])[C:27]1[CH:32]=[CH:31][CH:30]=[C:29](Br)[CH:28]=1>C1(C)C=CC=CC=1.O.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.CCO>[CH3:24][O:25][C:26]([C:27]1[CH:28]=[C:29]([C:6]2[CH:7]=[CH:8][C:9]([O:13][CH3:14])=[C:10]([O:11][CH3:12])[C:5]=2[O:4][CH3:3])[CH:30]=[CH:31][CH:32]=1)=[O:34]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 12070Methyl 3-bromobenzoateHCID 27735822,3,4-Trimethoxybenzeneboronic acid

Produkt 1

HCID 161162902',3',4'-Trimethoxy-biphenyl-3-carboxylic acid methyl esterAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 702EthanolLösungsmittel
HCID 962WaterLösungsmittel2×
HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

(The following reaction is done in an N2 atmosphere.) To a solution of 2,3,4-Trimethoxyphenylboronic acid (32) (1.40 g, 6.60 mmol) in toluene (15.0 mL) is added EtOH (2.0 mL), Pd(PPh3)4 (208 mg, 0.18 mmol) and Na2CO3.10 H2O (4.81 g, 16.80 mmol) in water (5.2 mL). The resulting mixture is carefully degassed (5 times alternating vacuum and flushing with N2). A solution of Methyl-3-bromobenzoate (9) (1.29 g, 6.00 mmol) in toluene (9.0 mL) is added by syringe, the resulting mixture is again carefully degassed and stirred overnight at 100° C. Partition the mixture between brine/EtOAc (1+1), separate layers, extract the aqu. layer with EtOAc (3×), wash the combined organic layer with brine, dry with Na2SO4 and remove solvent. Purify crude product by preparative radial chromatography (silica gel, EtOAc/CyH 1+5) to obtain 2′,3′,4′-Trimethoxy-biphenyl-3-carboxylic acid methyl ester (33) as a yellowish oil (1.07 g, 58%). 1H NMR (400 MHz, CDCl3): 3.66 (s, 3H); 3.89 (s, 3H); 3.92 (s, 6H); 6.74 (d, 1H, J=8.6 Hz); 7.03 (d, 1H, J=8.6 Hz); 7.44 (t, 1H, J=7.8 Hz); 7.70 (d, 1H, J=7.6 Hz); 7.97 (d, 1H, J=7.8 Hz); 8.15 (br.s 1H).

Aufarbeitung

  1. custom(The following reaction
  2. customThe resulting mixture is carefully degassed
  3. custom(5 times alternating vacuum and flushing with N2)
  4. customthe resulting mixture is again carefully degassed
  5. customPartition the mixture between brine/EtOAc (1+1)
  6. customseparate layers
  7. extractionextract the aqu
  8. washlayer with EtOAc (3×), wash the combined organic layer with brine
  9. dry with materialdry with Na2SO4
  10. customremove solvent
  11. customPurify crude product by preparative radial chromatography (silica gel, EtOAc/CyH 1+5)

Quellen und Nachweise

ORD-Eintrag
ord-ced4e8b5a80e470384169f170c44b174
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08394835B2

Notizen zur Reaktion

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