Methanol → (4-Bromo-1-benzofuran-2-yl)methanol

HRID 1740299Notes

Reaction equation

HRID 1740299 reaction equation
[Br:1][C:2]1[C:10]2[CH:9]=[C:8]([C:11](OCC)=[O:12])[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CO.C(OCC)(=O)C>O1CCCC1.O>[Br:1][C:2]1[C:10]2[CH:9]=[C:8]([CH2:11][OH:12])[O:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 21838105Ethyl 4-bromobenzofuran-2-carboxylate

Product 1

HCID 21838195(4-Bromo-1-benzofuran-2-yl)methanolYield 85.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-ethoxycarbonylbenzo[b]furan (0.5 g) in tetrahydrofuran (5 ml) was slowly added sodium borohydride (0.21 g) at room temperature. After 5 minutes, methanol (0.5 ml) was added thereto dropwise. The reaction mixture was stirred at room temperature for one hour and then ethyl acetate and water were added thereto. The mixture was adjusted to pH 5, and the layers were separated. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated to afford 4-bromo-2-hydroxymethylbenzofuran (0.36 g).

Workup

  1. customat room temperature
  2. customthe layers were separated
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-179e804997134bb38fc491fcedaf0224
Source dataset
uspto-grants-1999_10
Patent number
US05968985

Reaction notes

Loading…