2-Methylallyl 2,3-difluoro-6-hydroxy-5-(2-methylallyl)benzoate → 5,6-difluoro-2,2-dimethyl-3H-benzofuran-7-carboxylic acid

HRID 1909586Notes

Reaction equation

HRID 1909586 reaction equation
[F:1][C:2]1[C:14]([F:15])=[CH:13][C:12]([CH2:16][C:17]([CH3:19])=[CH2:18])=[C:11]([OH:20])[C:3]=1[C:4]([O:6]CC(C)=C)=[O:5]>C(O)=O>[F:15][C:14]1[C:2]([F:1])=[C:3]([C:4]([OH:6])=[O:5])[C:11]2[O:20][C:17]([CH3:19])([CH3:18])[CH2:16][C:12]=2[CH:13]=1

Participants

3

Reactant 1

HCID 585663922-Methylallyl 2,3-difluoro-6-hydroxy-5-(2-methylallyl)benzoate

Product 1

HCID 585663065,6-difluoro-2,2-dimethyl-3H-benzofuran-7-carboxylic acidYield 61%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 2-methylallyl 2,3-difluoro-6-hydroxy-5-(2-methylallyl)benzoate (734) in 96% formic acid (15 mL) was refluxed for 22 hours. The solvent was removed in vacuo, and the residue was purified by flash column chromatography eluting with hexanes-EtOAc (3:1) to afford 5,6-difluoro-2,2-dimethyl-3H-benzofuran-7-carboxylic acid (735) (0.76 g, 61%). 1H NMR (400 MHz, DMSO-d6) δ 7.43 (t, J=9.2 Hz, 1H), 2.98 (s, 2H), 1.41 (s, 6H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash column chromatography
  3. washeluting with hexanes-EtOAc (3:1)

Sources & evidence

ORD record
ord-2cff8e6916554318afe15af4be4b4c6f
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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