Cesium carbonate → Methyl 4'-hydroxy-3',5'-dimethylbiphenyl-4-carboxylate

HRID 222077

Reaktionsgleichung

Reaktionsgleichung von HRID 222077
[CH3:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[C:4]([CH3:17])[C:3]=1[OH:18].Br[C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:18][C:3]1[C:4]([CH3:17])=[CH:5][C:6]([C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=2)=[CH:7][C:2]=1[CH3:1]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 12081Methyl 4-bromobenzoateHCID 27346492,6-Dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Produkt 1

HCID 57747356Methyl 4'-hydroxy-3',5'-dimethylbiphenyl-4-carboxylateAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 2,6-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (525 mg, 2.12 mmol), methyl 4-bromobenzoate (460 mg, 2.14 mmol), PdCl2(dppf) (80 mg, 0.11 mmol) and Cs2CO3 (1.40 g, 4.31 mmol) in DMF (10 mL, 5% H2O) was heated at 80° C. for 1 h. The reaction mixture was diluted with EtOAc (50 mL), washed with H2O (2×50 mL), and dried over Na2SO4. Purification on a silica gel column gave the desired product as a pale yellow solid (430 mg). NMR (CDCl3): δ 8.08 (d, 2H), 7.62 (d, 2H), 7.29 (s, 2H), 4.75 (s, 1H), 3.95 (s, 3H), 2.35 (s, 6H).

Aufarbeitung

  1. washwashed with H2O (2×50 mL)
  2. dry with materialdried over Na2SO4
  3. customPurification on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-a99bbe64883849d3a055f9f4c1cdcac1
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207178B2

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