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

HRID 581971Notes

Reaction equation

HRID 581971 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[N+:8]([C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9].C(=O)([O-])[O-].[K+].[K+]>COCCOC.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:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:15]2[CH:16]=[C:11]([N+:8]([O-:10])=[O:9])[CH:12]=[CH:13][CH:14]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 122863-Bromopyridine

Product 1

HCID 121813273-(3-Nitrophenyl)pyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To 3-bromopyridine (8.53 g, 54 mmol) in ethyleneglycol dimethylether (180 ml) is added 3-nitrophenylboronic acid (10 g, 59.95 mmol), aqueous potassium carbonate (90 ml, 2M) and tetrakis(triphenylphosphine)palladium (0.5 g, 0.43 mmol). The mixture is refluxed gently in a nitrogen atmosphere overnight. The cooled reaction mixture is filtered and water (600 ml) is added to the filtrate. The precipitate is filtered off and washed with water. This crude product is dissolved in hot water (400 ml) with addition of hydrochloric acid (25 ml, 4 M). The mixture is filtered while still hot. The filtrate is cooled in an ice bath and pure 3-(3-pyridyl)-nitrobenzene is precipitated by addition of 12 M NaOH. Yield 9.14 g (85%).

Workup

  1. temperatureThe mixture is refluxed gently in a nitrogen atmosphere overnight
  2. customThe cooled reaction mixture
  3. filtrationis filtered
  4. additionwater (600 ml) is added to the filtrate
  5. filtrationThe precipitate is filtered off
  6. washwashed with water
  7. dissolutionThis crude product is dissolved in hot water (400 ml) with addition of hydrochloric acid (25 ml, 4 M)
  8. filtrationThe mixture is filtered while still hot
  9. temperatureThe filtrate is cooled in an ice bath
  10. custompure 3-(3-pyridyl)-nitrobenzene is precipitated by addition of 12 M NaOH

Sources & evidence

ORD record
ord-851bdc98a05f45ab83a3a14d1520ddc8
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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