Ethyl Acetate → 3-Bromo-4-(trifluoromethyl)benzenemethanamine

HRID 887288Notes

Reaction equation

HRID 887288 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Br:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[C:17]([F:20])([F:19])[F:18])[C:11]([NH2:13])=O.C(OCC)(=O)C.[OH-].[Na+]>C1COCC1.C(OCC)C>[Br:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[C:17]([F:18])([F:19])[F:20])[CH2:11][NH2:13]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 223376733-Bromo-4-(trifluoromethyl)benzamide

Product 1

HCID 223376523-Bromo-4-(trifluoromethyl)benzenemethanamine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

LiAlH4 (0.906 g, 23.9 mmol) was suspended in 60 mL of dry THF and cooled to 0° C. The mixture was treated with the product from Example 243B (3.2 g, 11.9 mmol) in THF (10 mL) dropwise with stirring. After 20 minutes, the mixture was warmed to room temperature 12 hours and treated in succession with ethyl acetate (2 mL), NaOH (50%, 5 mL), and diethyl ether (100 mL). The organic phase decanted, dried (Na2SO4), filtered and the filtrate was concentrated under reduced pressure to provide the title compound.

Workup

  1. temperaturethe mixture was warmed to room temperature 12 hours
  2. customThe organic phase decanted
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f091d0243ba040ad9b84c1805eec4adf
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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