Sulfuric Acid → 3,4-Difluoro-2-(difluoromethoxy)aniline

HRID 1275929ノート

反応式

HRID 1275929 の反応式
S(=O)(=O)(O)O.[F:6][C:7]1[C:8]([O:17][CH:18]([F:20])[F:19])=[C:9]([N+:14]([O-])=O)[CH:10]=[CH:11][C:12]=1[F:13]>[Fe].O>[F:6][C:7]1[C:8]([O:17][CH:18]([F:19])[F:20])=[C:9]([CH:10]=[CH:11][C:12]=1[F:13])[NH2:14]

参加物

5

反応物 2

HCID 1118Sulfuric AcidHCID 221180133-(Difluoromethoxy)-1,2-difluoro-4-nitro-benzene

生成物 1

HCID 221180113,4-Difluoro-2-(difluoromethoxy)aniline収率 72.8%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
95 °C

実験手順

Into a 200-ml four-necked flask provided with a reflux condenser, a thermometer and a stirrer were fed 7.0 g (0.125 mol) of an iron powder, 50 ml of water and 0.1 ml of 98% sulfuric acid. The resulting mixture was heated to 95° C. on an oil bath. Thereto was dropwise added, at 95 to 100° C. over 10 minutes, 11.3 g (0.05 mol) of the previously synthesized 3,4-difluoro-2-difluoromethoxy-nitrobenzene. The resulting mixture was stirred at the same temperature for 2.5 hours. Then, a Dean-Stark trap was fitted and the mixture was refluxed with heating, whereby an oily substance was separated as a fraction of azeotropic distillation with water. The aqueous layer was subjected to extraction with 100 ml of methylene chloride. The resulting methylene chloride layer was mixed with the oily substance. The resulting mixture was concentrated, and the resulting residue was subjected to vacuum distillation to obtain 7.1 g (yield: 72.8%) of 3,4-difluoro-2-difluoromethoxy-aniline (purity: 99.1%, boiling point: 76-78° C./6 mmHg).

後処理

  1. customInto a 200-ml four-necked flask provided with a reflux condenser
  2. additionThereto was dropwise added, at 95 to 100° C. over 10 minutes
  3. customThen, a Dean-Stark trap was fitted
  4. temperaturethe mixture was refluxed
  5. temperaturewith heating
  6. customwhereby an oily substance was separated as a fraction of azeotropic distillation with water
  7. extractionThe aqueous layer was subjected to extraction with 100 ml of methylene chloride
  8. additionThe resulting methylene chloride layer was mixed with the oily substance
  9. concentrationThe resulting mixture was concentrated
  10. distillationthe resulting residue was subjected to vacuum distillation

出典と根拠

ORDレコード
ord-ff8e5457f53e4f71a831f514fc7c7aac
出典データセット
uspto-grants-2000_12
特許番号
US06162944

反応ノート

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