Water → 3-Bromo-4-fluorobenzaldehyde

HRID 231318

反応式

HRID 231318 の反応式
S(=O)(=O)(O)O.O.[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:11][OH:12].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[K+].[K+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C(Cl)Cl>[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[F:16])[CH:11]=[O:12]

参加物

7

反応物 4

HCID 962Water2 回HCID 1118Sulfuric AcidHCID 24502Potassium DichromateHCID 27733513-Bromo-4-fluorobenzyl Alcohol

生成物 1

HCID 1736043-Bromo-4-fluorobenzaldehyde収率 81%

試薬・触媒・溶媒 2

HCID 21218Trioctylmethylammonium chloride触媒HCID 6344Dichloromethane溶媒

実験手順

A misture of 29.4 g (0.3 mol) of sulphuric acid, 50 ml of water and 2 ml of Aliquat 336 (tricapryl-methyl-ammonium chloride) was added to a solution of 20.5 g (0.1 mol) of 3-bromo-4-fluoro-benzyl alcohol in 250 ml of methylene chloride at room temperature. Thereafter, 9.7 g (0.033 mol) of potassium dichromate were added to the reaction mixture and the temperature was kept at about 25° C. for 2 hours by cooling slightly. After adding 100 ml of water, the organic phase was separated off and the aqueous phase was extracted once more with 100 ml of methylene chloride. The organic phases were washed twice with 100 ml of water each time, then once with 100 ml of saturated sodium bicarbonate solution and once more with 100 ml of water, dried over sodium sulphate and evaporated in vacuo. The residue was distilled. 16.3 g (81% of theory) of 3-bromo-4-fluoro-benzaldehyde were obtained in this manner as a colorless oil with a boiling point of 65° C./0.3 mm Hg.

後処理

  1. temperatureby cooling slightly
  2. customthe organic phase was separated off
  3. extractionthe aqueous phase was extracted once more with 100 ml of methylene chloride
  4. washThe organic phases were washed twice with 100 ml of water each time
  5. dry with materialonce with 100 ml of saturated sodium bicarbonate solution and once more with 100 ml of water, dried over sodium sulphate
  6. customevaporated in vacuo
  7. distillationThe residue was distilled

出典と根拠

ORDレコード
ord-dbf6db348254410585d2e7e63a02f66c
出典データセット
uspto-grants-1989_07
特許番号
US04845249

関連ノート

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