2,3-Dichloropyridine → 4-(3-Chloropyridin-2-yl)benzoic acid

HRID 1391429Notes

Reaction equation

HRID 1391429 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1B(O)O)([OH:3])=[O:2].Cl[C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[CH:16][N:15]=1>C([O-])([O-])=O.[K+].[K+].C(#N)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.[Pd]>[Cl:20][C:19]1[C:14]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=2)=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 2

HCID 169882,3-DichloropyridineHCID 27339852-(Dihydroxyboranyl)benzoic acid

Product 1

HCID 221704544-(3-Chloropyridin-2-yl)benzoic acid

Reagents, catalysts & solvents 3

HCID 178527696HCID 178527696, compoundCatalystHCID 6342AcetonitrileSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
90 °C

Procedure

Tetrakis palladium (0.1 2 g, 0.1 mMol) was added to a suspension of carboxybenzene boronic acid (0.33 g, 2.0 mMol) and 2,3-dichloropyridine (0.296 g, 2.0 mMol) in a mixture of 0.4M K2CO3 (10 mL) and acetonitrile (10 mL) and the mixture was heated at 90° C. for 12 hrs under a blanket of nitrogen. The hot suspension was filtered, the filtrate concentrated to about half the original volume before being washed with methylene chloride. The aq. layer was carefully acidified with conc. HCl and the precipitate was collected, washed with water and vacuum dried to obtain the product as a white solid.

Workup

  1. filtrationThe hot suspension was filtered
  2. concentrationthe filtrate concentrated to about half the original volume
  3. washbefore being washed with methylene chloride
  4. customthe precipitate was collected
  5. washwashed with water and vacuum
  6. customdried

Sources & evidence

ORD record
ord-64fd27ecb3c84abc97072bb50d7e3fc8
Source dataset
uspto-grants-2008_03
Patent number
US07338950B2

Reaction notes

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