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

HRID 29454Notes

Reaction equation

HRID 29454 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][CH3:16].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][CH3:16]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 687165365-Bromo-4-methoxy-3-methyl-benzofuran-2-carboxylic acid

Product 1

HCID 68711184(5-Bromo-4-methoxy-3-methyl-benzofuran-2-yl)-methanolYield 81.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromo-4-methoxy-3-methyl-benzofuran-2-carboxylic acid (286 mg, 1.0 mmol, 1 eq, Example 119, Step 3)) in 5 mL of THF under a nitrogen atmosphere was placed in a water bath. To this solution, 1.4 mL of BH3.THF (1.0 M in THF, 1.4 mmol, 1.4 eq) was added dropwise. After 24 h the reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with water, saturated sodium carbonate and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo to give (5-bromo-4-methoxy-3-methyl-benzofuran-2-yl)-methanol (220 mg) in 81% yield. 1H NMR (400 MHz, CDCl3) δ ppm 2.4 (s, 3 H) 3.9 (s, 3 H) 4.7 (s, 2 H) 7.1 (d, J=8.6 Hz, 1 H) 7.4 (d, J=8.8 Hz, 1 H).

Workup

  1. customAfter 24 h the reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, saturated sodium carbonate and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c1a3fe6dc2f94facb6ef4d75f8968d82
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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