Toluene → 5-(4-Hydroxy-2-methyl-phenyl)-benzofuran-2-carboxylic acid ethyl ester

HRID 250277

Reaktionsgleichung

Reaktionsgleichung von HRID 250277
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12](Br)=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2].C[C:17]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[CH:19][C:18]=1[OH:32].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:41]1(C)C=CC=CC=1>C1COCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2(OC)CC=CC(OC)=C2C2C=CC=CC=2)CCCCC1>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:14]=[CH:13][C:12]([C:21]3[CH:22]=[CH:17][C:18]([OH:32])=[CH:19][C:20]=3[CH3:41])=[CH:11][C:9]=2[CH:10]=1)=[O:5])[CH3:2]

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 735184Ethyl (5-bromobenzofuran)-2-carboxylateHCID 513583382-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Produkt 1

HCID 672715765-(4-Hydroxy-2-methyl-phenyl)-benzofuran-2-carboxylic acid ethyl esterAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 665453372-Dicyclohexylphosphino-2,6-dimethoxybiphenylKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A solution of 5-bromo-benzofuran-2-carboxylic acid ethyl ester (275 mg, 1.02 mmol) and 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (239 mg, 1.11 mmol) in toluene (5.0 mL) and THF (5.0 mL) is added to a flask. The flask is evacuated and re-filled with N2 three times. Pd(OAc)2 (5 mg, 0.022 mmol) and 2-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl (20 mg, 0.049) and potassium phosphate, tribasic, N-hydrate (432 mg, 2.04 mmol) are added and the mixture is heated at 85° C. for 8 hours. The reaction mixture is cooled to room temperature and filtered through a pad of diatomaceous earth. The filtrate is concentrated to a residue which is purified by silica gel chromatography eluting with 20-30% EtOAc/Hexanes to provide the title compound (179 mg, 56%). ES/MS m/e 297.0 (M+1), 295.0 (M−1).

Aufarbeitung

  1. customThe flask is evacuated
  2. additionre-filled with N2 three times
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationfiltered through a pad of diatomaceous earth
  5. concentrationThe filtrate is concentrated to a residue which
  6. customis purified by silica gel chromatography
  7. washeluting with 20-30% EtOAc/Hexanes

Quellen und Nachweise

ORD-Eintrag
ord-aa7bed7c608a4062abad4592f270c584
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863302B2

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