o-Bromo-nitrostyrene → 2-Bromophenethylamine

HRID 380178

Reaction equation

HRID 380178 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][N+:6]([O-])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].OS([O-])(=O)=O.[K+]>C1COCC1>[Br:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH2:4][CH2:5][NH2:6]

Participants

5

Reactant 3

HCID 187792o-Bromo-nitrostyreneHCID 516920Potassium bisulfateHCID 21226445Aluminium lithium hydride

Product 1

HCID 27340912-Bromophenethylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the styrene of Step 1 (0.310 g, 1.3 mmol) in 5 mL of THF was added 1 M LiAlH4 solution in THF (5.2 mL, 5.2 mmol) at 0° C. The solution was stirred for 1 hour. A concentrated KHSO4 solution was added dropwise to destroy the excess of LiAlH4. The solution was filtered over celite and the filtrate concentrated in vacuo to give a yellow oil; 150 mg (58%).

Workup

  1. customto destroy the excess of LiAlH4
  2. filtrationThe solution was filtered over celite
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give a yellow oil

Sources & evidence

ORD record
ord-ab63b32f4e8645a9b7debf98a5dabaaf
Source dataset
uspto-grants-2001_10
Patent number
US06300501B1

Linked notes

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