Water → (5-Bromo-1-benzofuran-2-yl)methanol

HRID 1916646Notes

Reaction equation

HRID 1916646 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16](OCC)=[O:17])=[CH:13][C:12]=2[CH:21]=1.O.[OH-].[Na+]>C1COCC1>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([CH2:16][OH:17])=[CH:13][C:12]=2[CH:21]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 735184Ethyl (5-bromobenzofuran)-2-carboxylateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 2795537(5-Bromo-1-benzofuran-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

7.0 mL (7.00 mmol) 1 M lithium aluminium hydride solution in THF is slowly added dropwise at −5° C. to a solution of 3.70 g (13.8 mmol) ethyl 5-bromo-benzofuran-2-carboxylate in 50 mL THF. The reaction solution is heated to RT and then cooled again to 10° C. Another 0.7 mL (0.70 mmol) 1 M lithium aluminium hydride solution in THF are added dropwise and the reaction is stirred for 1 h at RT. 1.0 mL water, 1.0 mL 15% NaOH and finally 3.0 mL water are added successively to the reaction mixture and the insoluble precipitate is filtered off. The organic phase is dried over MgSO4, filtered through activated charcoal and the solvent is eliminated i.vac.

Workup

  1. temperaturecooled again to 10° C
  2. filtrationthe insoluble precipitate is filtered off
  3. dry with materialThe organic phase is dried over MgSO4
  4. filtrationfiltered through activated charcoal

Sources & evidence

ORD record
ord-c7cb7ebf53084f62916839f8d0211ce5
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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