Hydrogen Bromide → HCID 19925668, compound

HRID 1647503Notes

Reaction equation

HRID 1647503 reaction equation
C([O:8][C:9]([C:11]1[CH:33]=[CH:32][C:14]([O:15][CH2:16][C:17]([C:19]2[O:20][C:21]3[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][C:22]=3[CH:23]=2)=[O:18])=[CH:13][CH:12]=1)=[O:10])C1C=CC=CC=1.Br>C(O)(=O)C>[C:28]([C:25]1[CH:26]=[CH:27][C:21]2[O:20][C:19]([C:17](=[O:18])[CH2:16][O:15][C:14]3[CH:13]=[CH:12][C:11]([C:9]([OH:10])=[O:8])=[CH:33][CH:32]=3)=[CH:23][C:22]=2[CH:24]=1)([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 19925685HCID 19925685, compound

Product 1

HCID 19925668HCID 19925668, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-(4-Benzyloxycarbonylphenoxyacetyl)-5-tert-butylbenzofuran (1 g) obtained in Example 13 was suspended in 15 ml of acetic acid and 2 ml of 47% hydrobromic acid and the mixture was stirred at 60° C. for 15 hours. The reaction mixture was cooled, poured into ice water, the mixture was extracted with ethyl acetate, the extract was washed with water, dried over anhydrous magnesium sulfate, concentrated in vacuo, ether was added to the residue and the mixture was filtered followed by recrystallization from acetonitrile to give 510 mg of crystals. M.p. 209.5°-211° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo, ether
  6. additionwas added to the residue
  7. filtrationthe mixture was filtered
  8. customfollowed by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-16f03299babc49cfbb2b5ba9ac1454f9
Source dataset
uspto-grants-1995_07
Patent number
US05432195

Reaction notes

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