3-Nitrophenylboronic Acid → 3-(3-Nitrophenyl)pyridine

HRID 1633595Notes

Reaction equation

HRID 1633595 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[C:14]1[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].C(O)CCO>O.C(COC)OC.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+:1]([C:4]1[CH:5]=[C:6]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 16773-Nitrophenylboronic AcidHCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 122863-Bromopyridine

Product 1

HCID 121813273-(3-Nitrophenyl)pyridineYield 84.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of 3-nitrophenylboronic acid (50 g, 0.3 mol), 3-bromopyridine (48 ml, 0.5 mol), potassium carbonate (207 g, 1.5 mol), 1,3-propanediol (107 ml, 1.5 mol) and tetrakis(triphenylphosphine)palladium(0) (0.5 g) in a mixture of water (200 ml) and dimethoxyethane (400 ml) was stirred in a nitrogen atmosphere at 80° C. for 3 hours. After cooling the dimethoxyethane was removed under reduced pressure and the residue was stirred with additionally 200 ml water overnight. The precipitate was filtered off and extracted with aqueous hydrochloric acid (4M, 300 ml). The extract was rendered alkaline by addition of aqueous sodium hydroxide (12M). The product was filtered off, washed with water and dried with suction to yield 3-(3-nitrophenyl)pyridine (50.6 g, 84%).

Workup

  1. customwas removed under reduced pressure
  2. stirringthe residue was stirred with additionally 200 ml water overnight
  3. filtrationThe precipitate was filtered off
  4. extractionextracted with aqueous hydrochloric acid (4M, 300 ml)
  5. additionby addition of aqueous sodium hydroxide (12M)
  6. filtrationThe product was filtered off
  7. washwashed with water
  8. customdried with suction

Sources & evidence

ORD record
ord-198c633cc0504075a3b277150aef8157
Source dataset
uspto-grants-2003_01
Patent number
US06503925B1

Reaction notes

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