Sodium Carbonate → 4'-Methoxy[1,1'-biphenyl]-4-sulfonic acid

HRID 1964798Notes

Reaction equation

HRID 1964798 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[Na].Br[C:14]1[CH:19]=[CH:18][C:17]([S:20]([O-:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O.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>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 86600836Sodium 4-bromobenzene-sulfonate

Product 1

HCID 234334014'-Methoxy[1,1'-biphenyl]-4-sulfonic acidYield 89.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4-methoxyphenylboronic acid (35 g, 0.23 mol), sodium-4-bromobenzene-sulfonate (50 g, 0.19 mol) and Na2CO3 (200 g) were taken in toluene (1000 ml) and water (500 ml). To this was added Pd(PPh3)4 (11 g, 0.011 mol) and the reaction mixture was refluxed for 12 h under N2 atmosphere. The reaction mixture was cooled, filtered off the solid residue, washed with toluene and acidified with 6N HCl. The solid precipitate was filtered and dried to give 4′-methoxy[1,1′-biphenyl]-4-sulfonic acid (45 g, 88%).

Workup

  1. temperaturethe reaction mixture was refluxed for 12 h under N2 atmosphere
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered off the solid residue
  4. washwashed with toluene
  5. filtrationThe solid precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-7c27cc6854294f1c9021336fa4b8f616
Source dataset
uspto-grants-2013_04
Patent number
US08415480B2

Reaction notes

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