Sodium Carbonate → Sodium 4-(pyridin-4-yl)benzoate

HRID 2244277Notes

Reaction equation

HRID 2244277 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].Cl.Br[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+:25].[Na+]>C(#N)C>[N:18]1[CH:19]=[CH:20][C:15]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:16][CH:17]=1.[Na+:25]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 881004-Bromopyridinium chlorideHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 23673507Sodium 4-(pyridin-4-yl)benzoateYield 18%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 4-carboxybenzeneboronic acid (0.660 g, 3.98 mmol) and 4-bromopyridine hydrochloride (0.770 g, 3.98 mmol) in dry acetonitrile (20 mL) was added 0.4 M aqueous sodium carbonate (20 mL) and the mixture was purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.240 g) was then added and the reaction mixture heated to 90° C. for 22 hours. The precipitated sodium salt was filtered, washed with acetonitrile and then dried in vacuo at 50° C. overnight to give the title compound (0.162 g, 18%) as a grey solid.

Workup

  1. customthe mixture was purged with nitrogen for 10 minutes
  2. additionTetrakis(triphenylphosphine)palladium(0) (0.240 g) was then added
  3. filtrationThe precipitated sodium salt was filtered
  4. washwashed with acetonitrile
  5. customdried in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-f034ba4266ab4165a3543e871f2cfbfd
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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