Acetonitrile → 5-Chloro-2-fluoro-N,N-dimethyl-4-nitrobenzenamine

HRID 1831492Notes

Reaction equation

HRID 1831492 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](F)[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[C:13]([O-])([O-])=O.[K+].[K+].[C:19](#[N:21])C>>[Cl:1][C:2]1[CH:7]=[C:6]([N:21]([CH3:19])[CH3:13])[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 101303301-Chloro-4,5-difluoro-2-nitrobenzene

Product 1

HCID 220522305-Chloro-2-fluoro-N,N-dimethyl-4-nitrobenzenamineYield 98%

Procedure

A solution of 1-chloro-4,5-difluoro-2-nitro-benzene (Preparation 1) (20.0 g, 103.3 mmol), K2CO3 (31.4 g, 227.3 mmol) and dimethyl amine. HCl (9.3 g, 113.6 mmol) in acetonitrile (200 mL) was heated to reflux for 2 h. The solution cooled to room temperature, quenched with water and extracted with ethyl acetate. The ethyl acetate layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo to give 22.1 g (98%) of 1-chloro-5-dimethylamino-4-fluoro-2-nitro-benzene: Crude 1H NMR (400 MHz, CDCl3): δ 7.83 (d, J=14.2 Hz, 1H), 6.72 (d, J=8.3 Hz, 1H), 3.09 (d, J=2.2 Hz, 6H), 3.77 (br s, 2H). The crude material was pure enough to carry on to the next step.

Workup

  1. temperatureto reflux for 2 h
  2. customquenched with water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b74717e27347465d8517fc9662884b7d
Source dataset
uspto-grants-2006_06
Patent number
US07067658B2

Reaction notes

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