Potassium Carbonate → 2-Benzyloxy-5-chloro-[1,1';2',1'']terphenyl-3''-carboxylic acid ethyl ester

HRID 269523

Reaction equation

HRID 269523 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2Br)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1B(O)O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.C(OCC)(=O)C.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>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[C:13]([C:28]3[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=3[O:26][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 41987402-Benzyloxy-5-chlorobenzeneboronic acidHCID 587309812'-Bromobiphenyl-3-carboxylic acid ethyl ester

Product 1

HCID 587309782-Benzyloxy-5-chloro-[1,1';2',1'']terphenyl-3''-carboxylic acid ethyl esterYield 47.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 882672-Methylphenethyl alcoholSolvent

Procedure

2′-Bromo-biphenyl-3-carboxylic acid ethyl ester (157 mg, 0.5 mmol), 2-benzyloxy-5-chloro-phenylboronic acid (157 mg, 0.6 mmol), tetrakis(triphenylphosphine)palladium(0) (66 mg, 0.06 mmol) and potassium carbonate (568 mg, 4.1 mmol) was heated in toluene-ethanol (1:1, 5 ml) at 90° C. for 4.5 hours. Upon cooling, the mixture was diluted with ethyl acetate and water. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography using Biotage with iso-hexane containing a gradient of ethyl acetate (1-5%) to yield the title compound (105 mg, 46%) as a white solid.

Workup

  1. temperatureUpon cooling
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-60e16d8cf406481789be8f046a7f0704
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Linked notes

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