Water → 3-Amino-1-(3-bromophenyl)butan-2-ol

HRID 517532Notes

Reaction equation

HRID 517532 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([OH:15])[CH:10]([N+:12]([O-])=O)[CH3:11])[CH:5]=[CH:6][CH:7]=1.O>CCO.[Fe]>[NH2:12][CH:10]([CH3:11])[CH:9]([OH:15])[CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1

Participants

5

Reactant 2

HCID 962WaterHCID 867114751-(3-Bromophenyl)-3-nitrobutan-2-ol

Product 1

HCID 823860203-Amino-1-(3-bromophenyl)butan-2-olYield 68.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(3-bromophenyl)-3-nitrobutan-2-ol (1.0 g, 3.6 mmol) in EtOH (20 mL)/H2O (1 mL), iron powder (2.0 g, 36 mmol) was added in one portion. The suspension was refluxed overnight, cooled to RT, and filtered. The filtrate was evaporated, diluted with H2O (30 mL), and extracted with EtOAc (50 mL×3). The organic layers were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=3:1) to afford 3-amino-1-(3-bromophenyl)butan-2-ol (600 mg, 68%). MS (ES+) C10H14BrNO requires: 243, 245 found: 244, 246[M+2+H]+(1:1).

Workup

  1. temperatureThe suspension was refluxed overnight
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. additiondiluted with H2O (30 mL)
  5. extractionextracted with EtOAc (50 mL×3)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=3:1)

Sources & evidence

ORD record
ord-0340d367f73349b7959fb17d4d28e168
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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