Dimethylformamide → 2,3-Dimethyl-5-phenyl-benzoic acid

HRID 1771833Notes

Reaction equation

HRID 1771833 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+].CN(C=O)C>CCO.CCOC(C)=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.O>[CH3:11][C:5]1[C:4]([CH3:12])=[CH:3][C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 668959895-Bromo-2,3-dimethylbenzoic acid

Product 1

HCID 894441102,3-Dimethyl-5-phenyl-benzoic acidYield 46.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-bromo-2,3-dimethyl-benzoic acid (690 mg, 3.0 mmol, 1.0 eq), phenylboronic acid (404 mg, 3.3 mmol, 1.1 eq) and Na2CO3 (958 mg, 9.0 mmol, 3.0 eq) in a mixture of EtOH (5 mL), DMF (20 mL) and water (5 mL) was added Pd(PPh3)4 (0.17 g, 0.15 mmol, 0.05 eq). The reaction was heated at 100° C. overnight then diluted with EtOAc and filtered through celite. The aqueous layer was acidified to pH 4-5 with diluted HCl and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue obtained was purified by column chromatography (petroleum ether:EtOAc, 10:1 then CH2Cl2:MeOH, 400:0 to 20:1) to give the title compound as a white solid (315 mg, 46%).

Workup

  1. filtrationfiltered through celite
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by column chromatography (petroleum ether

Sources & evidence

ORD record
ord-b3bc182074c74af0adeae3d3b6888f4f
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

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