2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Benzofuran

HRID 1913923Notes

Reaction equation

HRID 1913923 reaction equation
COC(/C=C/[C:7]1[CH:12]=[C:11](O)[C:10]2[O:14][CH:15](C3C=CC(O)=C(O)C=3)[CH:16](C(OC)=O)[C:9]=2[CH:8]=1)=O.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl>[O:14]1[C:10]2[CH:11]=[CH:12][CH:7]=[CH:8][C:9]=2[CH:16]=[CH:15]1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 5857314Dihydrobezofuran

Product 1

HCID 9223BenzofuranYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of dihydrobezofuran a (Davies, H. M. L.; Grazini, M. V. A.; Aouad, E. Org. Lett. 2001, 3, 1475) (160 mg, 0.9 mmol) DDQ (300 mg) and CH2Cl2 (11 mL) was maintained at room temp. for 2 days. The solution was diluted with 50% ethyl acetate-hexanes and washed with 0.5 N NaOH (3×10 mL), brine (1×10 mL), dried (Na2SO4), filtered, and concentrated to afford 150 mg (93%) of bezofuran b.

Workup

  1. washwashed with 0.5 N NaOH (3×10 mL), brine (1×10 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9ad138640d7645c385595cf6c8216756
Source dataset
uspto-grants-2013_12
Patent number
US08609845B2

Reaction notes

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