Hydrogen Bromide → 3-Cyano-2,4-dichloro-5-fluorobromobenzene

HRID 47906

反応式

HRID 47906 の反応式
[C:1]([C:3]1[C:4]([Cl:12])=[C:5]([CH:7]=[C:8]([F:11])[C:9]=1[Cl:10])N)#[N:2].Cl.O.N([O-])=O.[Na+].O.[BrH:20]>>[C:1]([C:3]1[C:4]([Cl:12])=[C:5]([Br:20])[CH:7]=[C:8]([F:11])[C:9]=1[Cl:10])#[N:2]

参加物

6

反応物 5

HCID 260Hydrogen BromideHCID 962WaterHCID 21885828Hydrate;hydrochlorideHCID 234317783-Cyano-2,4-dichloro-5-fluoroanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 234317903-Cyano-2,4-dichloro-5-fluorobromobenzene収率 86.2%

反応条件

温度
2.5 °C

実験手順

47.2 g of 3-cyano-2,4-dichloro-5-fluoroaniline (0.23 mol) were added to a solution of 150 ml of hydrochloric acid-water (1:1). The resulting mixture was stirred to be a slurry and then cooled to 0-5° C. A solution of sodium nitrite (16.7 g, 0.242 mol) and water (46 ml) was added thereto over 30 minutes. The resulting solution was added to a solution of cuprous bromide (0.275 mol) in 147 ml of hydrobromic acid. The reaction mixture was stirred for 2 hours and allowed overnight. The resulting mixture was wet-distilled. The distilled fraction was extracted with toluence. The oil layer was washed successively with 10% aqueous solution of NaOH, concentrated sulfuric acid and water, and dried over anhydrous sodium sulfate. After removing the solvent, the residue was crystallized from toluene to give 53.3 g of 3-cyano-2,4-dichloro-5-fluorobromobenzene (0.198 mol) in 86.2% yield.

後処理

  1. stirringThe reaction mixture was stirred for 2 hours
  2. waitallowed overnight
  3. distillationThe resulting mixture was wet-distilled
  4. extractionThe distilled fraction was extracted with toluence
  5. washThe oil layer was washed successively with 10% aqueous solution of NaOH, concentrated sulfuric acid and water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removing the solvent
  8. customthe residue was crystallized from toluene

出典と根拠

ORDレコード
ord-f6ad75e6f33a41e3a3fc7e6b19cfe702
出典データセット
uspto-grants-2004_03
特許番号
US06699992B2

関連ノート

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