3-Nitrophenylboronic Acid → 4-(3-nitrophenyl)pyridine

HRID 479995Notes

Reaction equation

HRID 479995 reaction equation
Cl.Br[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=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-].[K+].[K+].C(O)CCO>C(COC)OC.O.C(OCC)(=O)C.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+:9]([C:12]1[CH:17]=[C:16]([C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[CH:15]=[CH:14][CH:13]=1)([O-:11])=[O:10]

Participants

9

Reactant 4

HCID 16773-Nitrophenylboronic AcidHCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 881004-Bromopyridinium chloride

Product 1

HCID 4595574-(3-nitrophenyl)pyridine

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-bromopyridine, hydrochloride (8.03; 41.3 mmol), 3-nitrophenylboronic acid (6.85 g; 41.0 mmol), potassium carbonate (34.2 g; 0.25 mol), 1,3-propandiol (14.9 ml; 0.21 mol) and 15 tetrakis(triphenylphosphine)palladium (0.2 g) in a mixture of dimethoxyethane (80 ml) and water (40 ml) was stirred at 80° C. in a nitrogen atmosphere overnight. The cooled mixture was diluted with ethyl acetate and filtered through celite. The filtrate was evaporated to dryness and water was added to the residue. Vigorously stirring caused the product to precipitate. The product was filtered off, washed with water, dried and 20 subsequently washed with petroleum ether. Yield: 8.15 g (99%).

Workup

  1. filtrationfiltered through celite
  2. customThe filtrate was evaporated to dryness and water
  3. additionwas added to the residue
  4. stirringVigorously stirring
  5. customto precipitate
  6. filtrationThe product was filtered off
  7. washwashed with water
  8. customdried
  9. wash20 subsequently washed with petroleum ether

Sources & evidence

ORD record
ord-3d027feb8576420ca9d704bb988757c8
Source dataset
uspto-grants-2003_11
Patent number
US06649609B2

Reaction notes

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