2,2'-Bipyridine → Sodium

HRID 1175058Notes

Reaction equation

HRID 1175058 reaction equation
Br[C:2]1[C:7]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][C:5]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:4][C:3]=1[S:16]([OH:19])(=[O:18])=[O:17].[Na:20].[Br:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1.N1C=CC=CC=1C1C=CC=CN=1>CC(N(C)C)=O.[Cu].O>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[C:7]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:6][C:5]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:4][C:3]=2[S:16]([OH:19])(=[O:18])=[O:17])=[CH:24][CH:23]=1.[Na:20]

Participants

9

Reactant 4

HCID 14742,2'-BipyridineHCID 115221-Bromo-4-iodobenzeneHCID 5360545SodiumHCID 19778783HCID 19778783, compound

Product 2

HCID 5360545SodiumHCID 86632270HCID 86632270, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2-bromo-benzene-1,3,5-trisulfonic acid, sodium salt and 1-bromo-4-iodo-benzene (1 equivalent) in DMAc can be treated with activated copper bronze (2.2 equivalents) and 2,2′-bipyridine (0.2 equivalents) then heated to 80° C. for 4 hours. The cooled mixture can be poured into water, the solids filtered off, and the filtrate evaporated and then dried under vacuum. The crude product can be isolated by extracting the solids with moist ethanol, filtering off the solids, and evaporating the filtrate to give 4′-bromo-biphenyl-2,4,6-trisulfonic acid, sodium salt.

Workup

  1. filtrationthe solids filtered off
  2. customthe filtrate evaporated
  3. customdried under vacuum
  4. customThe crude product can be isolated
  5. extractionby extracting the solids with moist ethanol
  6. filtrationfiltering off the solids
  7. customevaporating the filtrate

Sources & evidence

ORD record
ord-a0afe3e0c07a4eb98719e8cc9d0c6413
Source dataset
uspto-grants-2010_11
Patent number
US07838594B2

Reaction notes

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