Toluene → 2'-Sulfamoyl-biphenyl-4-carboxylic acid

HRID 2104424Notes

Reaction equation

HRID 2104424 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[C:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([OH:14])=[O:13].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.C(OCC)C>[NH2:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:18]1[CH:19]=[CH:20][C:15]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1)(=[O:10])=[O:9]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 28012632-Bromobenzenesulfonamide

Product 1

HCID 27605552'-Sulfamoyl-biphenyl-4-carboxylic acidYield 57.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

2-Bromobenzenesulfonamide (800 mg) and 4-carboxyphenyl boronic acid (563 mg) were suspended in a solvent mixture of toluene (5 mL) and water (5 mL). To the reaction mixture, tetrakis(triphenylphosphine)palladium (392 mg) and sodium carbonate anhydrate (1.08 g) were sequentially added, and the resultant mixture was heated under reflux overnight. The resultant mixture was cooled to room temperature, and diethyl ether and water were added thereto for partitioning the mixture. The organic layer was extracted twice with water. All the resultant aqueous layers were combined together, and 12N aqueous hydrochloric acid was added thereto to acidfy. The mixture was concentrated to about 20 mL under reduced pressure, and the precipitated colorless powder was recovered by filtration, followed by drying under reduced pressure, to thereby give the title compound (539 mg).

Workup

  1. temperatureunder reflux overnight
  2. customfor partitioning the mixture
  3. extractionThe organic layer was extracted twice with water
  4. addition12N aqueous hydrochloric acid was added
  5. concentrationThe mixture was concentrated to about 20 mL under reduced pressure
  6. filtrationthe precipitated colorless powder was recovered by filtration
  7. customby drying under reduced pressure

Sources & evidence

ORD record
ord-821e131802084aee9690a390e474d853
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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