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

HRID 2110735Notes

Reaction equation

HRID 2110735 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-52350acb93e247428b6d89927b833fe4
Source dataset
uspto-grants-2009_04
Patent number
US07517889B2

Reaction notes

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