Borane;tetrahydrofuran → (5-Bromo-4-isopropoxy-3-methyl-1-benzofuran-2-yl)methanol

HRID 29475Notes

Reaction equation

HRID 29475 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](O)=[O:11])=[C:7]([CH3:13])[C:6]=2[C:14]=1[O:15][CH:16]([CH3:18])[CH3:17].B.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][OH:11])=[C:7]([CH3:13])[C:6]=2[C:14]=1[O:15][CH:16]([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 687122265-Bromo-4-isopropoxy-3-methyl-benzofuran-2-carboxylic acid

Product 1

HCID 68714044(5-Bromo-4-isopropoxy-3-methyl-1-benzofuran-2-yl)methanolYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromo-4-isopropoxy-3-methyl-1-benzofuran-2-carboxylic acid (0.43 g 1.37 mmole) in 25 mL of THF under nitrogen was placed in a water bath. To this solution was added 2 mL of BH3.THF (1.0M in THF, 2.06 mmole, 1.4 eq) dropwise. After 24 hours, The mixture was quenched with water, the solvent was concentrated in vacuo, and the residue was extracted with ethyl acetate. The organic layer washed with water, saturated sodium carbonate and brine, dried over sodium sulfate, filtered, and concentrated to provide 0.33 g of (5-bromo-4-isopropoxy-3-methyl-1-benzofuran-2-yl) methanol. Yield 80.5%; EA: Theory C: 52.15: H, 5.05. Found C: 52.26; H: 4.80.

Workup

  1. customThe mixture was quenched with water
  2. concentrationthe solvent was concentrated in vacuo
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer washed with water, saturated sodium carbonate and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-db237c4f99c140729927dd1a0a70c4b6
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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