Metaperiodic acid → 4-[4-(Difluoromethyl)phenoxy]-6-(ethoxycarbonyl)-1-benzofuran-2-carboxylic acid

HRID 1177293Notes

Reaction equation

HRID 1177293 reaction equation
I(O)(=O)(=O)=[O:2].[F:6][CH:7]([F:31])[C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[C:18]3[CH:19]=[C:20]([CH:22]=[O:23])[O:21][C:17]=3[CH:16]=[C:15]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:14]=2)=[CH:10][CH:9]=1>CC#N.C(OCC)(=O)C.C1C=CC(N=NC2C=CC(N)=NC=2N)=CC=1.Cl.[Cr](F)([O-])(=O)=O>[F:31][CH:7]([F:6])[C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[C:18]3[CH:19]=[C:20]([C:22]([OH:2])=[O:23])[O:21][C:17]=3[CH:16]=[C:15]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:14]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 65185Metaperiodic acidHCID 59559912Ethyl 4-[4-(difluoromethyl)phenoxy]-2-formyl-1-benzofuran-6-carboxylate

Product 1

HCID 595601994-[4-(Difluoromethyl)phenoxy]-6-(ethoxycarbonyl)-1-benzofuran-2-carboxylic acidYield 96%

Reagents, catalysts & solvents 3

HCID 178479089HCID 178479089, compoundCatalystHCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To acetonitrile (10 mL) was added periodic acid (209 mg, 0.916 mmol) and stirred vigorously at room temperature for 15 min. Ethyl 4-[4-(difluoromethyl)phenoxy]-2-formyl-1-benzofuran-6-carboxylate (300 mg, 0.833 mmol) was then added (in ice-bath) followed by addition of pyridium fluorochromate (3.32.mg, 0.02 mmol) in CH3CN (5 mL). The reaction was stirred at 0° C. for 1 hour. The reaction was diluted with ethyl acetate and washed with brine/water (1:1), dried over MgSO4 and concentrated to give the title compound (300 mg, 96%) as an orange solid, which was used in the next step without further purification. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.33 (t, J=7.16 Hz, 3 H) 4.33 (q, J=7.16 Hz, 2 H) 6.61 (t, J=56.52 Hz, 1 H) 7.06 (d, J=8.48 Hz, 2 H) 7.37 (s, 1 H) 7.43-7.54 (m, 3 H) 8.02 (s, 1 H).

Workup

  1. stirringThe reaction was stirred at 0° C. for 1 hour
  2. washwashed with brine/water (1:1)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c9de5e291ee64117989edf70ab19047c
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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