Potassium Carbonate → Tert-butyl-3-(4-tolyl)benzoate

HRID 1018967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1018967
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.[C:11]([O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19](I)[CH:18]=1)([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>COCCOC.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>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:24])[CH:22]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 79799Tolylboronic acidHCID 18386959tert-Butyl 3-iodobenzoate

Produkt 1

HCID 18398672Tert-butyl-3-(4-tolyl)benzoateAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 4-methylphenylboronic acid (0.65 g, 4.3 mmol), t-butyl-3-iodobenzoate (0.87 g, 2.86 mmol), K2CO3 (0.59 g, 4.3 mmol), and (Ph3P)4 Pd (0.17 g, 0.14 mmol) in DME (15 mL) was degassed and flushed with N2 before being brought to reflux for 2 h. Following a standard aqueous/EtOAc work-up, the residue was triturated with 1:10 EtOAc/hexane. The excess boronic acid was removed by filtration, and the filtrate was concentrated to give an oil which was purified by flash chromatography (hexane) to give an oil (0.6 g). This material (≈60% pure) was used as such for the next step.

Aufarbeitung

  1. customwas degassed
  2. customflushed with N2
  3. temperatureto reflux for 2 h
  4. customthe residue was triturated with 1:10 EtOAc/hexane
  5. customThe excess boronic acid was removed by filtration
  6. concentrationthe filtrate was concentrated
  7. customto give an oil which
  8. customwas purified by flash chromatography (hexane)

Quellen und Nachweise

ORD-Eintrag
ord-8b042612c06344d6a445f3356df15688
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06486141B2

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