Ethanol → Ethyl 2-(4-bromobutyl)benzofuran-6-carboxylate

HRID 1732574Notes

Reaction equation

HRID 1732574 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[O:7][C:8]2[CH:14]=[C:13]([C:15]([OH:17])=[O:16])[CH:12]=[CH:11][C:9]=2[CH:10]=1.S(=O)(=O)(O)O.[CH2:23](O)[CH3:24]>>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[O:7][C:8]2[CH:14]=[C:13]([C:15]([O:17][CH2:23][CH3:24])=[O:16])[CH:12]=[CH:11][C:9]=2[CH:10]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 203039332-(4-Bromobutyl)benzofuran-6-carboxylic acid

Product 1

HCID 20303934Ethyl 2-(4-bromobutyl)benzofuran-6-carboxylate

Procedure

A solution of 2-(4-bromobutyl)benzofuran-6-carboxylic acid (29.7 g., 0.1 mole) and sulfuric acid (0.5 ml.) in ethanol (200 ml.) is boiled under reflux. The solution is concentrated to 7/8 volume at reduced pressure. The residue is poured into water. The oily ester is extracted with ether. Evaporation of the solvent provides ethyl 2-(4-bromobutyl)benzofuran-6-carboxylate.

Workup

  1. temperatureunder reflux
  2. concentrationThe solution is concentrated to 7/8 volume at reduced pressure
  3. additionThe residue is poured into water
  4. extractionThe oily ester is extracted with ether
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-8b34fd0874c848dea8e0bd04e0369885
Source dataset
uspto-grants-1980_12
Patent number
US04238487

Reaction notes

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