(5-bromo-1-benzofuran-2-yl)(phenyl)methanone → (5-Bromo-1-benzofuran-2-yl)(phenyl)methanol

HRID 364011Notes

Reaction equation

HRID 364011 reaction equation
[BH4-].[Na+].[C:3]([C:11]1[O:12][C:13]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:14]=2[CH:15]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>O.O1CCOCC1>[Br:20][C:17]1[CH:18]=[CH:19][C:13]2[O:12][C:11]([CH:3]([C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[OH:10])=[CH:15][C:14]=2[CH:16]=1

Participants

5

Reactant 2

HCID 801609(5-bromo-1-benzofuran-2-yl)(phenyl)methanoneHCID 4311764Sodium borohydride

Product 1

HCID 3067860(5-Bromo-1-benzofuran-2-yl)(phenyl)methanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4 g of sodium borohydride dissolved in the minimum quantity of water are slowly added at ambient temperature to 8.5 g of 2-benzoyl-5-bromobenzofuran in 50 ml of dioxane. When the addition is finished, the mixture is kept stirring at ambient temperature for a further 3 hours. The solvent is removed under reduced pressure, the residue is redissolved in 50 ml of water, and extracted with ethyl ether. The ether phase is dried with anhydrous sodium sulphate, evaporated to dryness, and leaves a residue which on crystallising from cyclohexane has a M.P. of 56°-58° C.

Workup

  1. additionWhen the addition
  2. customThe solvent is removed under reduced pressure
  3. dissolutionthe residue is redissolved in 50 ml of water
  4. extractionextracted with ethyl ether
  5. dry with materialThe ether phase is dried with anhydrous sodium sulphate
  6. customevaporated to dryness
  7. customleaves a residue which
  8. customon crystallising from cyclohexane

Sources & evidence

ORD record
ord-46de489a1ecf414fa6f1625c1d6f89df
Source dataset
uspto-grants-1986_08
Patent number
US04604392

Reaction notes

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