Hydrochloric Acid → (5-Bromo-1-benzofuran-2-yl)methanol

HRID 1603890Notes

Reaction equation

HRID 1603890 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](OCC)=[O:11])=[CH:7][C:6]=2[CH:15]=1.[BH4-].[Na+].O.Cl>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[CH:7][C:6]=2[CH:15]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 735184Ethyl (5-bromobenzofuran)-2-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 2795537(5-Bromo-1-benzofuran-2-yl)methanolYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5-bromo-2-benzofurancarboxylate (2.20 g, 8.19 mmol) in tetrahydrofuran (75 ml) was added with sodium borohydride (1.24 g) and some drops of water. The mixture was refluxed under stirring for 18 h and, after that, was added with some drops of concentrated HCl. The volatiles were evaporated off and the resulting residue was diluted with water and extracted with ethyl ether (3×75 ml). After drying and evaporating off the solvent under reduced pressure, a crude was obtained which was purified by chromatography through a silica gel column, eluting with petroleum ether:chloroform, 60:40. 1.19 g of the title product were recovered as a white solid with melting point 101-103° C. (64% yield).

Workup

  1. temperatureThe mixture was refluxed
  2. customThe volatiles were evaporated off
  3. additionthe resulting residue was diluted with water
  4. extractionextracted with ethyl ether (3×75 ml)
  5. customAfter drying
  6. customevaporating off the solvent under reduced pressure
  7. customa crude was obtained which
  8. customwas purified by chromatography through a silica gel column
  9. washeluting with petroleum ether
  10. custom1.19 g of the title product were recovered as a white solid with melting point 101-103° C. (64% yield)

Sources & evidence

ORD record
ord-c5756ea9fb5f442ea0e7e65ab5fb3a88
Source dataset
uspto-grants-1999_11
Patent number
US05990142

Reaction notes

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