Water → 3-Bromo-2-methyl-6-methylsulfonylbenzaldoxime

HRID 554689ノート

反応式

HRID 554689 の反応式
[N:1](OCCCC)=[O:2].[CH3:8][C:9]1[C:14]([CH3:15])=[C:13]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:12]=[CH:11][C:10]=1[Br:20].CC(C)([O-])C.[K+].O>CN(C)C=O.C(O)(=O)C>[Br:20][C:10]1[C:9]([CH3:8])=[C:14]([C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][CH:11]=1)[CH:15]=[N:1][OH:2]

参加物

7

反応物 4

HCID 962WaterHCID 10996Butyl nitriteHCID 187572522,3-Dimethyl-4-methylsulfonylbromobenzeneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 734619443-Bromo-2-methyl-6-methylsulfonylbenzaldoxime

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

A solution of 2.1 g (20 mmol) of n-butyl nitrite (97%) and 4 g (15 mmol) of 2,3-dimethyl-4-methylsulfonylbromobenzene in 50 ml of dimethylformamide is cooled to from −55 to −60° C., and a solution of 2.8 g (25 mmol) of potassium tert-butoxide in 35 ml of dimethylformamide is added dropwise at this temperature, over a period of 20 minutes. The reaction is monitored by HPLC. For work-up, initially 10 ml of water are added, and the mixture is then adjusted to pH 5-6 using about 9 ml of glacial acetic acid. The mixture is then poured onto 100 ml of ice-water and the aqueous phase is extracted with methylene chloride. The organic phase is washed with sodium bicarbonate solution, dried over magnesium sulfate and concentrated. This gives 3.6 g of an oily crude product (90% by HPLC) which can be purified by recrystallization from toluene.

後処理

  1. extractionthe aqueous phase is extracted with methylene chloride
  2. washThe organic phase is washed with sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThis gives 3.6 g of an oily crude product (90% by HPLC) which can be purified by recrystallization from toluene

出典と根拠

ORDレコード
ord-3587f9d2a47c4b4fb37857e5828c0e5b
出典データセット
uspto-grants-2011_11
特許番号
US08049017B2

反応ノート

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