Water → (E)-2-(4-benzofuran-2-ylphenyl)ethenesulfonic acid

HRID 2283261Notes

Reaction equation

HRID 2283261 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[S:10]([O:13]CC)(=[O:12])=[O:11])=[CH:4][CH:3]=1.[O:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)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>[O:16]1[C:17]2=[CH:18][CH:19]=[CH:24][C:23]2=[CH:22][CH:21]=[C:20]1[C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][C:5]=1/[CH:8]=[CH:9]/[S:10]([OH:13])(=[O:11])=[O:12]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 866320021-Bromo-4-[(E)-2-ethoxysulfonylethenyl]benzene

Product 1

HCID 86632001(E)-2-(4-benzofuran-2-ylphenyl)ethenesulfonic acid

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1-Bromo-4-[(E)-2-ethoxysulfonylethenyl]benzene (1.0 g, 3.4 mmol) and benzofuran-2-boronic acid (0.61 g, 3.7 mmol) were dissolved in DMF (20 mL). Sodium carbonate (2M, 10 mL) and tetrakis(triphenylphosphine)palladium(0) (200 mg, 0.17 mmol) were added and the resulting mixture was stirred under argon at 90° C. for 12 h. Water was added to the mixture and the resulting precipitate was collected, washed with water and dried to give the product as a sodium salt which was used in the next step without further purification (0.38 g, 35%).

Workup

  1. customthe resulting precipitate was collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-6f7934a3cfb64b659960316d4ee6f006
Source dataset
uspto-grants-2015_09
Patent number
US09145380B2

Reaction notes

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