Water → HCID 58251652, compound

HRID 37755Notes

Reaction equation

HRID 37755 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1.[CH:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][C:15]=1[C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].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.C1(C)C=CC=CC=1.O1CCCC1>[CH3:13][O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:27]2[CH:26]=[CH:25][C:24]([C:15]3[CH:16]=[CH:17][C:18]4[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:14]=3)=[CH:29][CH:28]=2)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1385211-Bromo-4-methoxynaphthaleneHCID 453822584-(2-Naphthyl)phenylboronic Acid

Product 1

HCID 58251652HCID 58251652, compoundYield 68.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-Bromo-4-methoxynaphthalene (25 g, 0.105 mol), 4-(naphthalen-2-yl)phenylboronic acid (30.4 g, 0.137 mol), potassium carbonate (21.9 g, 0.16 mol), tetrakis(triphenylphosphine)palladium(0) (2.4 g, 0.01 mol), water (25 mL), tetrahydrofuran (75 mL) and toluene (75 mL) were stirred in a 250 mL round-bottom flask for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (300 mL) and water (1000 mL). The organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The resulting solid was dissolved in hot toluene (400 mL) and filtered. The filtrate was recrystallized in methanol (800 mL). The resultant solid was filtered and washed with hexane (300 mL) to obtain a product (26 g, 0.072 mol, 68.4%).

Workup

  1. temperatureunder reflux
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate (300 mL) and water (1000 mL)
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe resulting solid was dissolved in hot toluene (400 mL)
  7. filtrationfiltered
  8. customThe filtrate was recrystallized in methanol (800 mL)
  9. filtrationThe resultant solid was filtered
  10. washwashed with hexane (300 mL)

Sources & evidence

ORD record
ord-a13ff7dac0f443fb964422a0af8d4114
Source dataset
uspto-grants-2013_09
Patent number
US08524381B2

Reaction notes

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