Bromine → 4-Bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)pyrrole-3-carbonitrile

HRID 1885371노트

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HRID 1885371 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:19])[C:10]([C:15]([F:18])([F:17])[F:16])=[CH:11][C:12]=2[C:13]#[N:14])=[CH:4][CH:3]=1.[Br:20]Br>ClC1C=CC=CC=1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH3:19])[C:10]([C:15]([F:18])([F:16])[F:17])=[C:11]([Br:20])[C:12]=2[C:13]#[N:14])=[CH:6][CH:7]=1

참가 물질

6

반응물 2

HCID 24408Bromine2회HCID 118221892-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

생성물 1

HCID 1835584-Bromo-2-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)pyrrole-3-carbonitrile수율 89.4%

시약·촉매·용매 3

HCID 962Water용매HCID 7964Chlorobenzene용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A solution of 2-(p-chlorophenyl)-1-methyl-5-(trifluoromethyl)pyrrole-3-carbonitrile (5.70 g, 0.02 mol) in chlorobenzene is treated with bromine (3.52 g, 0.022 mol), heated at 80° C. for 20 hours, cooled to room temperature, treated with additional bromine (3.52 g, 0.022 mol) and heated at 100° C. until reaction is complete by HPLC analysis. The reaction mixture is cooled to room temperature and diluted with ethyl acetate and water. The organic phase is washed with aqueous sodium metabisulfite, dried (MgSO4) and concentrated in vacuo to afford a solid residue. The residue is recrystallized from ethyl acetate/heptane to give the title product as a white solid, 6.50 g (89.4% yield), mp 126°-129° C.

후처리

  1. temperaturecooled to room temperature
  2. temperatureheated at 100° C. until reaction
  3. temperatureThe reaction mixture is cooled to room temperature
  4. washThe organic phase is washed with aqueous sodium metabisulfite
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto afford a solid residue
  8. customThe residue is recrystallized from ethyl acetate/heptane

출처 및 근거

ORD 기록
ord-eecfa46de4a149aabb45ebe0dcb1230c
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05144041

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