3-Nitrophenylboronic Acid → HCID 15541135, compound

HRID 1384971Notes

Reaction equation

HRID 1384971 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=1.[N+:11]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)([O-:13])=[O:12].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.[Pd].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>[N+:11]([C:14]1[CH:19]=[C:18]([C:2]2[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([CH3:10])[CH:3]=2)[CH:17]=[CH:16][CH:15]=1)([O-:13])=[O:12]

Participants

7

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 169194-Bromo-2,6-dimethylphenol

Product 1

HCID 15541135HCID 15541135, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4-bromo-2,6-dimethylphenol (2.58 g, 12.8 mmol) and 3-nitrophenylboronic acid (2.08 g, 12.5 mmol) in toluene (50 mL) were added tetrakis(triphenylphosphine)palladium(0) (0.48 g, 0.42 mmol) and 2M sodium carbonate (6.3 mL, 13 mmol). The mixture was stirred at 100° C. for 22 hours at which time additional palladium catalyst (150 mg) was added. The mixture was heated for another 20 hours and then cooled to room temperature. The mixture was partitioned between water and ethyl acetate. The organic layer was dried and concentrated. The residue was purified on silica gel, eluting with 12% ethyl acetate in hexanes, to provide 4-(3-nitrophenyl)-2,6-dimethylphenol as a yellow solid (0.932 g, 31%).

Workup

  1. additionwas added
  2. temperatureThe mixture was heated for another 20 hours
  3. customThe mixture was partitioned between water and ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel
  7. washeluting with 12% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-8b50271708f14412a9d19804418a11aa
Source dataset
uspto-grants-2001_07
Patent number
US06262078B1

Reaction notes

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