1-(2,2-Diethoxyethoxy)-4-fluorobenzene → 5-Fluoro-1-benzofuran

HRID 1405269Notes

Reaction equation

HRID 1405269 reaction equation
C(O[CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)C>C1C=CC=CC=1>[F:13][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 114475181-(2,2-Diethoxyethoxy)-4-fluorobenzene

Product 1

HCID 117883225-Fluoro-1-benzofuran

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of benzene (200 mL) containing polyphosphoric acid (80 g, 236.69 mmol) was added 2-(4-fluoro-phenoxy)-acetaldehyde diethyl acetal (45 g, 197.37 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 a silica gel column (1% ethyl acetate in petroleum ether) to afford 5-fluorobenzofuran as colorless oil (14.0 g, crude).

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 a silica gel column (1% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-74f37c4d505c405db126133124508b91
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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