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Water → Ethyl 3''-tert-butyl-4''-diethylamino-4'-hydroxy[1,1';3',1'']terphenyl-4-carboxylate

HRID 1158148
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1158148
Br[C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].[C:20]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][C:29]=1[N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].O>C1(C)C=CC=CC=1.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>[C:20]([C:24]1[CH:25]=[C:26]([C:2]2[CH:3]=[C:4]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=3)[CH:5]=[CH:6][C:7]=2[OH:8])[CH:27]=[CH:28][C:29]=1[N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])([CH3:23])([CH3:21])[CH3:22]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 16657517Ethyl 3'-bromo-4'-hydroxybiphenyl-4-carboxylateHCID 666718773-Tert-butyl-4-diethylaminophenylboronic acid

Produkt 1

HCID 11676663Ethyl 3''-tert-butyl-4''-diethylamino-4'-hydroxy[1,1';3',1'']terphenyl-4-carboxylateAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To 5.6 g of ethyl 3′-bromo-4′-hydroxy-biphenyl-4-carboxylate (17 mmol) are added 6.5 g of 3-tert-butyl-4-diethylaminophenylboronic acid (26 mmol) dissolved in 112 mL of toluene and 30.5 mL of 2M potassium carbonate (61 mmol). The reaction medium is stirred and heated to 40° C.; 2 g of tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (1.74 mmol) are added and the medium is heated to 110° C. and stirred for 3 hours. The reaction is stopped by adding 200 mL of water and the medium is then extracted with 200 mL of ethyl acetate. The organic phases are washed with 400 mL of water and neutralized with 200 mL of saturated NH4Cl and then dried over magnesium sulfate. The solvents are evaporated off and the residue is then purified by chromatography on silica gel (eluent: 9/1 heptane/ethyl acetate). 1.2 g of ethyl 3″-tert-butyl-4″-diethylamino-4′-hydroxy[1,1′;3′,1″]terphenyl-4-carboxylate are obtained (yield=16%) in the form of an orange solid.

Aufarbeitung

  1. temperaturethe medium is heated to 110° C.
  2. stirringstirred for 3 hours
  3. extractionthe medium is then extracted with 200 mL of ethyl acetate
  4. washThe organic phases are washed with 400 mL of water and neutralized with 200 mL of saturated NH4Cl
  5. dry with materialdried over magnesium sulfate
  6. customThe solvents are evaporated off
  7. customthe residue is then purified by chromatography on silica gel (eluent: 9/1 heptane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-9fb914ea5dbd4e3aab90dd3f19e57117
Quelldatensatz
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07807708B2

Notizen zur Reaktion

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