Trifluoroacetic acid → 4-(2,3-Dihydrobenzofuran-2-yl)benzoic acid

HRID 1501079Notes

Reaction equation

HRID 1501079 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[C:10]1[CH:22]=[CH:21][C:13]([C:14]([O:16]C(C)(C)C)=[O:15])=[CH:12][CH:11]=1.FC(F)(F)C(O)=O>ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1[C:10]1[CH:11]=[CH:12][C:13]([C:14]([OH:16])=[O:15])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89580836Tert-butyl 4-(2,3-dihydrobenzofuran-2-yl)benzoate

Product 1

HCID 895805944-(2,3-Dihydrobenzofuran-2-yl)benzoic acidYield 83.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2,3-dihydrobenzofuran-2-yl)benzoate (0.03 g, 0.1 mmol) in dichloromethane (3.0 mL) was added trifluoroacetic acid (1.0 mL). The reaction mixture was stirred at room temperature for 1 hour. After the reaction, the solvent was removed in vacuo, and the mixture was dissolved in dichloromethane (50 mL), washed with water (50 mL). The organic phase was dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo to give pure product 4-(2,3-dihydrobenzofuran-2-yl)benzoic acid as a white solid (0.02 g, 80%).

Workup

  1. customAfter the reaction
  2. customthe solvent was removed in vacuo
  3. dissolutionthe mixture was dissolved in dichloromethane (50 mL)
  4. washwashed with water (50 mL)
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ccc2940771514635911eb9482d83b1a6
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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