Potassium Carbonate → HCID 59314180, compound

HRID 1047799Notes

Reaction equation

HRID 1047799 reaction equation
I[C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:12](/B(O)O)=[CH:13]\[CH3:14].C([O-])([O-])=O.[K+].[K+]>CCO.[Pd]>[CH3:11][C:10]1[C:2](/[CH:12]=[CH:13]/[CH3:14])=[C:3]([CH:7]=[CH:8][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27593652-Iodo-3-methylbenzoic acidHCID 6157276((1E)-prop-1-en-1-yl)boronic acid

Product 1

HCID 59314180HCID 59314180, compoundYield 105.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To a solution of 2-iodo-3-methyl-benzoic acid (708 mg, 2.70 mmol) and trans-1-propen-1-ylboronic acid (526 mg, 6.12 mmol) in EtOH (10 mL) is added palladium anchored homogeneous catalyst, FibreCatPd(0) (4.84% Pd, 235 mg, 0.15 mmol) and 2M aqueous solution of K2SO4 (3.06 mL, 6.12 mmol). The resulting reaction mixture is covered with argon and run in a microwave reaction: 110° C., 7 h. After concentration in vacuo, the residue is purified by HPLC to give a pure product (162) as a pale yellow solid (500 mg, 93%).

Workup

  1. customThe resulting reaction mixture
  2. customrun in a microwave reaction
  3. custom110° C., 7 h
  4. concentrationAfter concentration in vacuo
  5. customthe residue is purified by HPLC

Sources & evidence

ORD record
ord-f06789a02071493bb1a4e3385c654709
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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