Sulfuric Acid → 3-Bromophenethylamine

HRID 1712943Notes

Reaction equation

HRID 1712943 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].S(=O)(=O)(O)O.[Br:12][C:13]1[CH:14]=[C:15]([CH2:19][C:20]#[N:21])[CH:16]=[CH:17][CH:18]=1.[OH-].[Na+]>C1COCC1.C(OCC)C.O>[Br:12][C:13]1[CH:14]=[C:15]([CH2:19][CH2:20][NH2:21])[CH:16]=[CH:17][CH:18]=1

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 36023(3-Bromophenyl)acetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 70217363-BromophenethylamineYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 2M LAH (31 mL) in THF (37 mL) at 0° C. was added sulfuric acid (1.6 mL) dropwise. This mixture was allowed to stir for 30 min and then (3-bromophenyl)-acetonitrile (30.6 mmol) in THF (7.5 mL) was slowly added. The reaction mixture was allowed to warm to rt and stir for 1 hr. The reaction was cooled to 0° C. and then a 1:1 v:v mixture of THF:water (20 mL) was added, followed by diethyl ether (40 mL). A precipitate formed. 4N NaOH was added until the solution reached pH=9. The mixture was filtered and the solid was washed with ether. The solution was dried over Na2SO4 and concentrated to give 2-(3-bromophenyl)ethanamine (28.1 mmol, 92%) as an oil, which was used without further purification.

Workup

  1. stirringstir for 1 hr
  2. temperatureThe reaction was cooled to 0° C.
  3. customA precipitate formed
  4. filtrationThe mixture was filtered
  5. washthe solid was washed with ether
  6. dry with materialThe solution was dried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-fa22d5ad63184c05aa734d76645dd8d7
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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