Potassium Phosphate, Tribasic → 2-(4-Hydroxyphenyl)naphthalene-1,4-dione

HRID 1958219Notes

Reaction equation

HRID 1958219 reaction equation
Br[C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[OH:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[OH:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[C:3](=[O:13])[C:4]3[C:9]([C:10](=[O:12])[CH:11]=2)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 749441,4-Naphthalenedione, 2-bromo-HCID 75806TricyclohexylphosphineHCID 27343604-Hydroxyphenylboronic acid

Product 1

HCID 117768692-(4-Hydroxyphenyl)naphthalene-1,4-dioneYield 45.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

An example compound, 2-(4-hydroxy-phenyl)-[1,4]naphthoquinone was synthesized in the following way. To a mixture of 2-bromo-1,4-naphthoquinone (1.0 g, 4.22 mmol), 4-hydroxy phenyl boronic acid (640 mg, 4.64 mmol), potassium phosphate (3.135 g, 14.76 mmol), tri cyclo hexyl phosphine (118 mg, 0.422 mmol), toluene (20 mL) and water (1 mL) was added palladium acetate (47 mg, 0.21 mmol) under nitrogen. The reaction mix was heated to ˜100° C. for 3 h and then cooled to room temperature. Water was added and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water, brine, dried and concentrated to give crude product, which was purified by column chromatography, using 10% ethyl acetate in hexane to give (480 mg, 45% yield) of 2-(4-Hydroxy-phenyl)-[1,4]naphthoquinone; MS (ES) m/z, 251.03 (M+1).

Workup

  1. customAn example compound, 2-(4-hydroxy-phenyl)-[1,4]naphthoquinone was synthesized in the following way
  2. additionThe reaction mix
  3. temperaturecooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water, brine
  7. customdried
  8. concentrationconcentrated
  9. customto give crude product, which
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-7cec4327350741d59d7ec75ce8915c4a
Source dataset
uspto-grants-2013_04
Patent number
US08410109B2

Reaction notes

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