2-Iodobenzoic acid → 2-(3-methylphenyl)benzoic Acid

HRID 1275732Notes

Reaction equation

HRID 1275732 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.I[C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15].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.COCCOC>[CH3:1][C:2]1[CH:3]=[C:4]([C:12]2[C:13]([C:14]([OH:16])=[O:15])=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 69412-Iodobenzoic acidHCID 10340Sodium CarbonateHCID 27339503-Tolylboronic acid

Product 1

HCID 43213212-(3-methylphenyl)benzoic AcidYield 41.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

In an oven dried flask flushed with N2 was combined 2.7 g (20.0 mmol) of 3-methylbenzeneboronic acid, 3.64 g (15 mmol) of 2-iodobenzoic acid, 150 mL of DME, 26 mL of 10% Na2CO3 and 600 mg (0.5 mmol) of Pd(PPh3)4. The mixture was warmed to reflux for 24 h and partitioned between 100 mL of NaHCO3 and 100 mL of ether. The ether layer was extracted with 2×50 mL of NaHCO3 and the combined NaHCO3 fractions were washed with 2×50 mL of ether, acidified with 10% HCl and extracted with 3×75 mL of ether. The combined ether extracts were washed with 50 mL of H2O, 50 mL of brine, dried (MgSO4) and concentrated in vacuo. The oil was crystallized from ether/hexanes (1/1) at -20° C. as a white precipitate, which after filtration, provided 1.32 g (41% yield) of 3'-methyl-2-biphenylcarboxylic acid as a brown oil.

Workup

  1. customIn an oven dried flask
  2. customflushed with N2
  3. temperatureThe mixture was warmed
  4. temperatureto reflux for 24 h
  5. custompartitioned between 100 mL of NaHCO3 and 100 mL of ether
  6. extractionThe ether layer was extracted with 2×50 mL of NaHCO3
  7. washthe combined NaHCO3 fractions were washed with 2×50 mL of ether
  8. extractionextracted with 3×75 mL of ether
  9. washThe combined ether extracts were washed with 50 mL of H2O, 50 mL of brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo
  12. customThe oil was crystallized from ether/hexanes (1/1) at -20° C. as a white precipitate, which
  13. filtrationafter filtration

Sources & evidence

ORD record
ord-6f64b40302d143dcbe66c49811c26b66
Source dataset
uspto-grants-2000_12
Patent number
US06162824

Reaction notes

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