Phenylboronic Acid → 5-Nitro-2-phenylpyridine

HRID 1500205Notes

Reaction equation

HRID 1500205 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>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.COCCOC>[C:11]1([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 66827Phenylboronic AcidHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 27628735-Nitro-2-phenylpyridineYield 97.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

2-Chloro-5-nitropyridine (3.0 g, 18.9 mmol), phenylboronic acid (2.5 g, 20.8 mmol), and tetrakis(triphenylphosphine)palladium (0.2 g, 0.2 mmol) were added to 1,2-dimethoxyethan (30 ml), then degassed and purged with nitrogen three times under reduced pressure. Under nitrogen atmosphere the mixture was stirred at room temperature for 20 minutes, then 1M aqueous sodium carbonate (40 ml) was poured in, and the temperature was raised to 80° C. After the reaction at 80° C. for 6 hours, the mixture was cooled to room temperature and crystallized with addition of water. The precipitated crystals were filtered to give the title compound (3.7 g, 96.8%).

Workup

  1. customdegassed
  2. custompurged with nitrogen three times under reduced pressure
  3. addition1M aqueous sodium carbonate (40 ml) was poured in, and the temperature
  4. temperaturewas raised to 80° C
  5. customAfter the reaction at 80° C. for 6 hours
  6. temperaturethe mixture was cooled to room temperature
  7. customcrystallized with addition of water
  8. filtrationThe precipitated crystals were filtered

Sources & evidence

ORD record
ord-61873d8c3f144894b90da7630caf2ccd
Source dataset
uspto-grants-2015_12
Patent number
US09206129B2

Reaction notes

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