Aluminium lithium hydride → 2-(3,4-Difluorophenyl)ethanamine

HRID 216207Notes

Reaction equation

HRID 216207 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][N+:10]([O-])=O)=[CH:4][C:3]=1[F:13].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[F:13][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][NH2:10])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 668019841,2-Difluoro-4-(2-nitroethenyl)benzene

Product 1

HCID 34669162-(3,4-Difluorophenyl)ethanamineYield 63.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 1,2-difluoro-4-(2-nitro-vinyl)benzene (1.5 g) in THF (50 mL) is added dropwise lithium aluminum hydride (23 mL, 1M in ether) and the solution is heated at 40° C. for 3 hours. The solution is cooled, diluted with ether and quenched with Na2SO4.10H2O (104 g) overnight. The solid is filtered, and the solution is evaporated in vacuo and chromatographed on silica gel eluting with EtOAc to afford 2-(3,4-difluoro-phenyl)-ethylamine (0.81 g). MS: 170 (M+H); 1H NMR (300 MHz, CDCl3) □6.9-7 (3H, m); 2.95 (2H, t); 2.7 (2H, t).

Workup

  1. temperatureThe solution is cooled
  2. customquenched with Na2SO4.10H2O (104 g) overnight
  3. filtrationThe solid is filtered
  4. customthe solution is evaporated in vacuo
  5. customchromatographed on silica gel eluting with EtOAc

Sources & evidence

ORD record
ord-318de45a473a440592e228334f63cd7b
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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