Tetrabutylammonium Fluoride → N-(4-Bromo-2-iodophenyl)benzenesulfonamide

HRID 400588

반응식

HRID 400588 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]1([S:25]([N:28](S(C2C=CC=CC=2)(=O)=O)[C:29]2[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:30]=2[I:36])(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1.C(OCC)(=O)C.Cl>[Br:35][C:32]1[CH:33]=[CH:34][C:29]([NH:28][S:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:27])=[O:26])=[C:30]([I:36])[CH:31]=1

참가 물질

6

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 60026850N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline)

생성물 1

HCID 60026307N-(4-Bromo-2-iodophenyl)benzenesulfonamide수율 90.2%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of tetrabutylammonium fluoride (1 M in THF, 11 mL) in 30 mL of THF was treated with N,N-bisbenzenesulfonyl-(4-bromo-2-iodoaniline) (5.78 g, 10 mmol) in several portions. After 18 hours, the mixture was diluted with of 40 mL of ethyl acetate and 40 mL of 1 N HCl. The phases were separated and the aqueous layer was extracted with two 40 mL portions of ethyl acetate. The combined organic layers were washed with two 20 mL portions of 1 N HCl, two 20 mL portions of saturated aqueous sodium bicarbonate solution, 20 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 3.95 g (90% yield) of the title compound as a solid, which was used without further purification.

후처리

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with two 40 mL portions of ethyl acetate
  3. washThe combined organic layers were washed with two 20 mL portions of 1 N HCl, two 20 mL portions of saturated aqueous sodium bicarbonate solution, 20 mL of brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f48f7c3ff64b4f578e03f54458b9a514
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

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