HCID 11688411, compound → HCID 21105712, compound

HRID 746428Notes

Reaction equation

HRID 746428 reaction equation
C1([O:6][C:7]2[C:12]3[O:13][C:14]4[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=4[C:11]=3[C:10]([CH:23]=[O:24])=[CH:9][CH:8]=2)CCCC1>Br.C(O)(=O)C>[OH:6][C:7]1[C:12]2[O:13][C:14]3[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=3[C:11]=2[C:10]([CH:23]=[O:24])=[CH:9][CH:8]=1

Participants

4

Reactant 1

HCID 11688411HCID 11688411, compound

Product 1

HCID 21105712HCID 21105712, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

4-cyclopentyloxy-8-nitro-1-formyl dibenzo[b,d]furan (200 mg, 0.530 mol) was heated in HBr (47% in acetic acid) (5 ml) in glacial acetic acid (10 ml) at 50° C. for 7-8 h. The reaction contents were poured in ice-water (200 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layer was washed with saturated sodium bicarbonate, and water and dried over anhydrous sodium sulfate. Removal of the organic solvent in vacuo afforded the crude product as a white solid (150 mg). The crude white solid was used as such without further purification. mp: >270° C.

Workup

  1. customThe reaction contents
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washThe combined organic layer was washed with saturated sodium bicarbonate, and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customRemoval of the organic solvent in vacuo

Sources & evidence

ORD record
ord-ac939750d3d4463b8b818cb53c767635
Source dataset
uspto-grants-2008_07
Patent number
US07393846B2

Reaction notes

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