3-Nitrophenylboronic Acid → HCID 85749594, compound

HRID 1595260Notes

Reaction equation

HRID 1595260 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[N+:21]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:9][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=2)=[CH:3][C:2]=1[C:28]1[CH:27]=[CH:26][CH:25]=[C:24]([N+:21]([O-:23])=[O:22])[CH:29]=1

Participants

8

Reactant 4

HCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 85749597Ethyl 3′-bromo-4′-methoxy[1,1′-biphenyl]-4-carboxylate

Product 1

HCID 85749594HCID 85749594, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 3′-bromo-4′-methoxy-[1,1′-biphenyl]-4-carboxylic acid, ethyl ester (26.6 g, 79.3 mmol), 3-nitrophenylboronic acid (21.2 g, 127 mmol), tri-o-tolylphosphine (2.51 g, 8.26 mmol), palladium (II) acetate (0.91 g, 4.05 mmol), potassium carbonate (21.9 g, 159 mmol) and water (100 mL) in dimethylformamide (400 mL) is heated at 60° C. for 2 h. The mixture is then treated with water (1000 mL) and extracted with ethyl acetate (3×200 mL). The combined extracts are dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by chromatography (silica gel, 10% ethyl acetate in cyclohexane) to give 4′-methoxy-3′-(3-nitrophenyl)-[1,1′-biphenyl]-4-carboxylic acid, ethyl ester as a colourless crystalline solid, m.p. 106-108° C.

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. dry with materialThe combined extracts are dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent is evaporated off under reduced pressure
  5. customto yield the crude product which
  6. customis purified by chromatography (silica gel, 10% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-861f352756734d04b7d2aeda055bd747
Source dataset
uspto-grants-2001_09
Patent number
US06288092B1

Reaction notes

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