Toluene → HCID 57879393, compound

HRID 1673373Notes

Reaction equation

HRID 1673373 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(=O)([O-])O.[Na+].C1(C)C=CC=CC=1.[C:25]([NH:33][CH:34]1[CH:43]=[CH:42][CH:41]=[CH:40][C:35]1(Br)[C:36]([O:38]C)=[O:37])(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>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(O)C>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:42]2[CH:41]=[CH:40][C:35]([C:36]([OH:38])=[O:37])=[C:34]([NH:33][C:25](=[O:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:43]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 37021224-Acetylphenylboronic acidHCID 67344810HCID 67344810, compound

Product 1

HCID 57879393HCID 57879393, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

51 mg of 4-acetylphenylboronic acid, 61 mg of sodium hydrogen carbonate and 12 mg of tetrakis(triphenylphosphine)palladium(0) were added to a mixed solution of 2.0 mL of toluene, 0.6 mL of ethanol and 0.4 mL of water containing 70 mg of methyl 2-(benzamido)-1-bromobenzoate, and stirred under pressure at 160° C. for 5 minutes. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration, ethyl acetate and 0.5 mol/L hydrochloric acid were added and a solid substance was separated by filtration. The obtained solid substance was added to a mixed solution of 1.0 mL of 2.0 mol/L aqueous sodium hydroxide and 5.0 mL of ethanol and stirred at room temperature for 1 hour and 30 minutes. 0.6 mol/L hydrochloric acid and ethyl acetate were added to the reaction mixture. The organic layer was separated, and the solvent was evaporated under reduced pressure to obtain 50 mg of 4-(4-acetylphenyl)-2-(benzamido)benzoic acid as white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. custominsoluble were removed by filtration, ethyl acetate and 0.5 mol/L hydrochloric acid
  3. additionwere added
  4. customa solid substance was separated by filtration
  5. additionThe obtained solid substance was added to a mixed solution of 1.0 mL of 2.0 mol/L aqueous sodium hydroxide and 5.0 mL of ethanol
  6. stirringstirred at room temperature for 1 hour and 30 minutes
  7. addition0.6 mol/L hydrochloric acid and ethyl acetate were added to the reaction mixture
  8. customThe organic layer was separated
  9. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-677650b646ba4243a4eecb89ce4551ed
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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