3-Nitrophenylboronic Acid → HCID 18667575, compound

HRID 1059936Notes

Reaction equation

HRID 1059936 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:10]([C:13]1[CH:14]=[C:15](B(O)O)[CH:16]=[CH:17][CH:18]=1)([O-:12])=[O:11].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.[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>[CH3:9][O:8][C:7]1[C:2]([C:17]2[CH:18]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=[CH:15][CH:16]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 10340Sodium CarbonateHCID 903642-Bromo-3-methoxypyridine

Product 1

HCID 18667575HCID 18667575, compoundYield 90.2%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 2-bromo-3-methoxypyridine (1.54 g), 3-nitrophenylboronic acid (1.77 g) and tetrakis(triphenylphosphine)-palladium (473 mg) in 1,2-dimethoxyethane (30 ml) was added 2M aqueous solution of sodium carbonate (10.6 ml). The mixture was stirred at 80° C. for 15 hours under a nitrogen atmosphere, then cooled to room temperature and diluted with ethyl acetate. 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 40 g, 25% ethyl acetate in n-hexane) to give 3-(3-methoxypyridin-2-yl)nitrobenzene (1.7 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 40 g, 25% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-da22cc7558d44855bba1e3b0e8acb799
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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