3-Nitrophenylboronic Acid → 2-(3-Nitrophenyl)naphthalene

HRID 2230962Notes

Reaction equation

HRID 2230962 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.OB(O)[C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=1>C1(C)C=CC=CC=1.CO.C(=O)([O-])[O-].[Na+].[Na+].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>[CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[C:14]1[CH:15]=[C:16]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 2

HCID 16773-Nitrophenylboronic AcidHCID 113722-Bromonaphthalene

Product 1

HCID 113226332-(3-Nitrophenyl)naphthaleneYield 89.7%

Reagents, catalysts & solvents 5

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-bromonaphthalene (5.0 g) and tetrakis(triphenylphosphine)palladium(0) (0.56 g) in toluene (50 ml) was added a solution of dihydroxy(3-nitrophenyl)borane (4.44 g) in methanol and 2M sodium carbonate solution in water (12 ml). The resulting mixture was stirred at 80° C. for 4 hours and extracted with ethyl acetate. After evaporation of the solvent, the crude residue was crystallized from hexane to give 3-(2-naphthyl)-1-nitrobenzene (5.4 g).

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter evaporation of the solvent
  3. customthe crude residue was crystallized from hexane

Sources & evidence

ORD record
ord-b8f0acea75694a8e8d1fcd770b27c495
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

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