Ethanol → 3-Bromobenzyl alcohol

HRID 326904Notes

Reaction equation

HRID 326904 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].CCO.[BH4-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 765833-BromobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 851413-Bromobenzyl alcohol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Bromobenzaldehyde (157 mmol) was dissolved in 300 mL of THF. At 0° C., 800 mL of EtOH was added, followed by NaBH4 (5.93 g, 157 mmol). The mixture was then stirred at r.t. (room temperature) for 1 hour and poured into cold 25% aq. (aqueous) NH4OAc. The organic solvents were evaporated and the residue was extracted with toluene:THF 1:1, dried over Na2SO4 and filtered through silica to yield the title compound.

Workup

  1. customThe organic solvents were evaporated
  2. extractionthe residue was extracted with toluene:THF 1:1
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered through silica

Sources & evidence

ORD record
ord-3f41e97ca4c6420db98ce8839491ae83
Source dataset
uspto-grants-1993_12
Patent number
US05270324

Reaction notes

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