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

HRID 1061106노트

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HRID 1061106 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f58738cff96c4cd0ae2379cbf83c16ce
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525204B1

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