Bromine → 3-Bromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]-2-[(trifluoromethyl)thio]pyrrole

HRID 1464673노트

반응식

HRID 1464673 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10]([S:20][C:21]([F:24])([F:23])[F:22])=[CH:11][C:12]=2[S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[CH:4][CH:3]=1.[Br:25]Br>C(Cl)(Cl)Cl.BrBr.C(Cl)Cl>[Br:25][C:11]1[C:12]([S:13]([C:16]([F:17])([F:19])[F:18])(=[O:15])=[O:14])=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[NH:9][C:10]=1[S:20][C:21]([F:24])([F:22])[F:23]

참가 물질

6

반응물 2

HCID 24408BromineHCID 189304062-(p-Chlorophenyl)-3-[(trifluoromethyl)sulfonyl]-5-[(trifluoromethyl)thio]pyrrole

생성물 1

HCID 189303903-Bromo-5-(p-chlorophenyl)-4-[(trifluoromethyl)sulfonyl]-2-[(trifluoromethyl)thio]pyrrole수율 41.9%

시약·촉매·용매 3

HCID 24408Bromine촉매HCID 6212Chloroform용매2회HCID 6344Dichloromethane용매

실험 절차

A solution of 2-(p-chlorophenyl)-3-[(trifluoromethyl)sulfonyl]-5-[(trifluoromethyl)thio]pyrrole (0.5 g, 0.00122 mol) in chloroform (10 mL) is cooled with an ice bath, treated with a solution of bromine (0.21 g, 0.00134 mol) in chloroform (5 mL), stirred for two hours, warmed to room temperature, treated with two drops of additional bromine and stirred for one hour. The reaction mixture is diluted with methylene chloride, washed with water, saturated sodium hydrogen carbonate solution, saturated sodium metabisulfite solution and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to obtain a syrup. Flash chromatography of the syrup using silica gel and a 1:5 ethyl acetate/hexanes solution gives the title product as a white solid (0.25 g, mp 122°-125° C.) which is identified by 1HNMR and 13CNMR spectral analyses.

후처리

  1. stirringstirred for one hour
  2. washwashed with water, saturated sodium hydrogen carbonate solution, saturated sodium metabisulfite solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a syrup

출처 및 근거

ORD 기록
ord-c24cdfa4d1f2413daed18bb5f6baad4f
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05306827

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