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

HRID 1070388Notes

Reaction equation

HRID 1070388 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.CC(C[AlH]CC(C)C)C.O>C1COCC1>[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

5

Reactant 3

HCID 962WaterHCID 14487Diisobutylaluminum hydrideHCID 735184Ethyl (5-bromobenzofuran)-2-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-bromo-benzofuran-2-carboxylate (5 g; 18.6 mmol) in 65 mL THF under nitrogen, was added DIBAL (46 mL, 46 mmol) dropwise over 30 minutes, then stirred overnight at room temperature. After dropwise addition of 25 mL of water, the mixture was evaporated, extracted with ethyl acetate, filtered, washed, dried (MgSO4) and evaporated to yield 4.2 g of crude product which was further purified by chromatography to afford (5-bromo-benzofuran-2-yl)-methanol.

Workup

  1. customthe mixture was evaporated
  2. extractionextracted with ethyl acetate
  3. filtrationfiltered
  4. washwashed
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto yield 4.2 g of crude product which
  8. customwas further purified by chromatography

Sources & evidence

ORD record
ord-f2e7841c5ebe4636a0f3340207c62eee
Source dataset
uspto-grants-2005_06
Patent number
US06903086B2

Reaction notes

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