Acetonitrile → 1-Chloro-5-dimethylamino-4-fluoro-2-nitro-benzene

HRID 1831492ノート

反応式

HRID 1831492 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

HCID 220522301-Chloro-5-dimethylamino-4-fluoro-2-nitro-benzene収率 98%

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b74717e27347465d8517fc9662884b7d
出典データセット
uspto-grants-2006_06
特許番号
US07067658B2

反応ノート

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