Sodium borohydride → 1-(5-Bromo-2-nitrophenyl)ethan-1-ol

HRID 230709Notes

Reaction equation

HRID 230709 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([Br:13])[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])(=[O:3])[CH3:2].[BH4-].[Na+]>O>[Br:13][C:6]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:4]([CH:1]([OH:3])[CH3:2])[CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 122241571-(5-Bromo-2-nitrophenyl)ethanone

Product 1

HCID 450733901-(5-Bromo-2-nitrophenyl)ethan-1-olYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 mmol of 3-acetyl-4-nitro-bromobenzene was placed in a 100 mL two-neck round-bottomed flask and dissolved in 30 mL of a solvent (ether), and then sodium borohydride was slowly added dropwise thereto in an ice bath. The reaction mixture was stirred at room temperature for 2 hours. After the completion of the reaction was confirmed by TLC, 5 mL of water was added to terminate the reaction and the precipitate was filtered off. The filtrate was washed twice with 30 mL of a sodium chloride solution, dried over anhydrous sodium sulfate, distilled under reduced pressure and purified by silica gel column chromatography (hexane/EtOAc=2/1) to obtain the desired 1-(5-bromo-2-nitrophenyl)ethanol as a yellow oil (71%).

Workup

  1. additionwas added
  2. customto terminate
  3. customthe reaction
  4. filtrationthe precipitate was filtered off
  5. washThe filtrate was washed twice with 30 mL of a sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled under reduced pressure
  8. custompurified by silica gel column chromatography (hexane/EtOAc=2/1)

Sources & evidence

ORD record
ord-d2bce80fbf8649df94b8ffd2b99ad22d
Source dataset
uspto-grants-2009_07
Patent number
US07566773B2

Reaction notes

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