HCID 58415336, compound → Benzofuran

HRID 2075161Notes

Reaction equation

HRID 2075161 reaction equation
C(O[CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10](SC2C=CC=CC=2)=[CH:9][CH:8]=1)C>C1C=CC=CC=1>[O:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH:4]=[CH:5]1

Participants

3

Reactant 1

HCID 58415336HCID 58415336, compound

Product 1

HCID 9223BenzofuranYield 169.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of (4-(2,2-Diethoxyethoxy)phenyl)(phenyl)sulfane (2.7 g, 8.5 mmol) and polyphosphoric acid (2.7 g, 27 mmol) in benzene (70 mL) was stirred at reflux for 2 h. The reaction mixture was cooled to room temperature, decanted from the PPA and filtered through a plug of silica gel, which was washed with hexanes. The filtrate and the wash were combined and concentrated under reduced pressure to yield 1.7 g (89%) of benzofuran: 1H NMR (400 MHz, CDCl3) δ 7.74 (d, 1H), 7.64 (dd, 1H), 7.49-7.39 (m, 2H), 7.29-7.16 (m, 5H), 6.74 (dd, 1H).

Workup

  1. temperatureat reflux for 2 h
  2. customdecanted from the PPA
  3. filtrationfiltered through a plug of silica gel, which
  4. washwas washed with hexanes
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-64712c1eec0346bd90b6de9e1acc55e8
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

Loading…