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Ethyl Acetate → (3-Bromo-4-(trifluoromethyl)phenyl)methanamine

HRID 586020
Notes
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Reaction equation

HRID 586020 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

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

Product 1

HCID 22337652(3-Bromo-4-(trifluoromethyl)phenyl)methanamine

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 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-1716085d81484645a245afb76626e37d
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06933311B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes