HCID 21429131, compound → 5-(Trifluoromethyl)-1-benzofuran

HRID 1403444Notes

Reaction equation

HRID 1403444 reaction equation
C(O[CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=1)C>C1C=CC=CC=1>[F:14][C:13]([F:16])([F:15])[C:10]1[CH:9]=[CH:8][C:7]2[O:6][CH:5]=[CH:4][C:12]=2[CH:11]=1

Participants

3

Reactant 1

HCID 21429131HCID 21429131, compound

Product 1

HCID 230580725-(Trifluoromethyl)-1-benzofuranYield 93.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of benzene (100 mL) containing polyphosphoric acid (19.45 g, 57.54 mmol) was added 1-(2,2-diethoxyethoxy)-4-(trifluoromethyl)benzene (8.0 g, 28.75 mmol). The mixture was stirred vigorously while being heated to reflux for 2.5 hours. The reaction mixture was cooled to room temperature and decanted from the polyphosphoric acid. The solvent was removed under vacuum to give the residue, which was purified by silica gel column chromatography eluting with 1% ethyl acetate in petroleum ether to afford 5-(trifluoromethyl)-1-benzofuran (5.0 g, crude) as colorless oil.

Workup

  1. temperaturewhile being heated
  2. temperatureto reflux for 2.5 hours
  3. customdecanted from the polyphosphoric acid
  4. customThe solvent was removed under vacuum
  5. customto give the residue, which
  6. customwas purified by silica gel column chromatography
  7. washeluting with 1% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-331556b1f664427c8f7048c63039d050
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

Loading…