Sodium Carbonate → 5-Bromo-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-2-ol

HRID 1846054Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846054
[CH2:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[C:8]([O:21][CH3:22])[CH:7]=1)(=[O:5])=[O:4])[CH3:2].[Br:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26](I)[CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.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>[Br:23][C:24]1[CH:29]=[C:28]([C:9]2[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH3:2])(=[O:4])=[O:5])=[CH:7][C:8]=2[O:21][CH3:22])[C:27]([OH:30])=[CH:26][CH:25]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 109245324-Bromo-2-iodophenolHCID 867232082-(4-(Ethylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 867232765-Bromo-4'-(ethylsulfonyl)-2'-methoxy-[1,1'-biphenyl]-2-olAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(4-(ethylsulfonyl)-2-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (Preparation 21, 600 mg, 1.84 mmol) in dioxane (30 mL) and water (10 mL) were added 4-bromo-2-iodophenol (604 mg, 2.02 mmol), sodium carbonate (488 mg, 4.6 mmol) and tetrakis(triphenylphosphine)palladium(0) (106 mg, 0.092 mmol). The reaction was stirred at reflux for 18 hours. The reaction was allowed to cool temperature and then filtered through celite. The filtrate was reduced to dryness and then purified by silica gel column chromatography eluting with cyclohexane:EtOAc 1:1 followed by a second silica gel column chromatography eluting with CH2Cl2:MeOH 98:2 to give the title compound as pale yellow solid in 44% yield, 301 mg.

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. temperatureto cool temperature
  3. filtrationfiltered through celite
  4. custompurified by silica gel column chromatography
  5. washeluting with cyclohexane:EtOAc 1:1
  6. washeluting with CH2Cl2:MeOH 98:2

Quellen und Nachweise

ORD-Eintrag
ord-05ed0762a00242b48bf17e1223ede3ed
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952008B2

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