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

HRID 1516631Notes

Reaction equation

HRID 1516631 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-2decdb1f495c4adcbe34209e793590ac
Source dataset
uspto-grants-2012_07
Patent number
US08227507B2

Reaction notes

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