3-Nitrophenylboronic Acid → HCID 611601, compound

HRID 1059907Notes

Reaction equation

HRID 1059907 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1)([O-:11])=[O:10].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.ClCCl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:8][C:7]1[C:2]([C:16]2[CH:17]=[C:12]([N+:9]([O-:11])=[O:10])[CH:13]=[CH:14][CH:15]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 2208322-Bromo-3-methylpyridine

Product 1

HCID 611601HCID 611601, compoundYield 84.5%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-bromo-3-methylpyridine (1.72 g), 3-nitrophenylboronic acid (2.17 g) and tetrakis(triphenylphosphine)-palladium (577 mg) in 1,2-dimethoxyethane (20 ml) was added 2M aqueous solution of sodium carbonate (13 ml). The mixture was stirred at 80° C. for 5 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with dichloromethane. The organic layer was separated, washed with water and brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 75g, dichloromethane:n-hexane=67:33 to 100:0) to give 3-(3-methylpyridin-2-yl)-nitrobenzene (1.81 g).

Workup

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 75g, dichloromethane:n-hexane=67:33 to 100:0)

Sources & evidence

ORD record
ord-4480220b4ec54819a1471978895cbdcc
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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