Water → 1-(5-Bromo-2-nitrophenyl)ethan-1-ol

HRID 1662942Notes

Reaction equation

HRID 1662942 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>CCOCC>[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

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 122241571-(5-Bromo-2-nitrophenyl)ethanone

Product 1

HCID 450733901-(5-Bromo-2-nitrophenyl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In an ice bath, about 10 mmols of 3-acetyl-4-nitro-bromobenzene was put into a 100 mL two-neck round flask, dissolved in about 30 mL solvent ether, and sodium borohydride was gradually added. The solution was stirred at room temperature for about 2 hours. After confirming reaction completion using TLC, reaction was completed by using about 5 mL water. The precipitate was filtered, and the filtered solution was washed twice with sodium chloride solution (about 30 mL). Then the washed solution was dried with sodium sulfate anhydride, and distilled under reduced pressure. Then, 1-(5-bromo-2-nitrophenyl)ethanol was obtained in a form of about 71% yellow oil using silica gel column chromatography (Hexane/EtOAc=2/1).

Workup

  1. customreaction completion
  2. customTLC, reaction
  3. filtrationThe precipitate was filtered
  4. washthe filtered solution was washed twice with sodium chloride solution (about 30 mL)
  5. dry with materialThen the washed solution was dried with sodium sulfate anhydride
  6. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-fe835b0527aa42208492638f15e4e440
Source dataset
uspto-grants-2011_10
Patent number
US08034747B2

Reaction notes

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