Sodium Carbonate → 2-[2-Fluoro-4-(furan-3-ylmethyl)-phenyl]propionic acid

HRID 1506872Notes

Reaction equation

HRID 1506872 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:14])[C:10]([O:12]C)=[O:11])=[C:5]([F:15])[CH:4]=1.[O:16]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17]1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.C1C(=O)[N-]C(=O)C1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Br[Pd+]>[F:15][C:5]1[CH:4]=[C:3]([CH2:2][C:18]2[CH:19]=[CH:20][O:16][CH:17]=2)[CH:8]=[CH:7][C:6]=1[CH:9]([CH3:14])[C:10]([OH:12])=[O:11]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 49837497Methyl 2-[4-(bromomethyl)-2-fluorophenyl]-propionate

Product 1

HCID 601555332-[2-Fluoro-4-(furan-3-ylmethyl)-phenyl]propionic acidYield 57.9%

Reagents, catalysts & solvents 2

HCID 11434313trans-Bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II)CatalystHCID 8028TetrahydrofuranSolvent

Procedure

Compound 20 (0.88 g, 3.2 mmol) and 3-furanboronic acid (0.54 g, 4.8 mmol) were dissolved in tetrahydrofuran (12 mL) and a 2 M-aqueous solution (4.0 mL) of sodium carbonate. To this solution, trans-bromo(N-succinimidyl)bis(triphenylphosphine)palladium(II) [trans-PdBr(N-Succ)(PPh3)2] (25.9 mg, 1.0 mol %) was added and treated in the same manner as in Example 11. The obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (20:1) solution followed by conventional hydrolysis with potassium hydroxide to give 0.46 g (55%) of compound (22a) of interest as white solid.

Workup

  1. additiontreated in the same manner as in Example 11
  2. washThe obtained residue was subjected to silica gel column chromatography and elution with an n-hexane/ethyl acetate (20:1) solution
  3. customfollowed by conventional hydrolysis with potassium hydroxide

Sources & evidence

ORD record
ord-0fd44c0358f444f1952c8d96788858f3
Source dataset
uspto-grants-2015_12
Patent number
US09221786B2

Reaction notes

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