Ethanol → HCID 14944863, compound

HRID 1505762Notes

Reaction equation

HRID 1505762 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1.[CH3:14][CH2:15]O>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 27947975-bromo-2,3-dihydrobenzofuran-7-carboxylic Acid

Product 1

HCID 14944863HCID 14944863, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 5-bromo-2,3-dihydro-1-benzofuran-7-carboxylic acid (1.0 g) in EtOH (15 mL), sulfuric acid (0.5 mL) was added, and the solution was heated at reflux for 30 hours. The reaction mixture was cooled to room temperature, and EtOH was removed. To the residue was added water, and the solution was extracted with ethyl acetate. The ethyl acetate layer was washed sequentially with saturated aqueous sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain the titled compound (1.07 g) as pale yellow powder.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 30 hours
  3. customEtOH was removed
  4. additionTo the residue was added water
  5. extractionthe solution was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed sequentially with saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-df5d4b1ac50d448987c4d82febe70205
Source dataset
uspto-grants-2015_12
Patent number
US09216968B2

Reaction notes

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