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

HRID 1885371ノート

反応式

HRID 1885371 の反応式
[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

参加物

6

反応物 2

HCID 24408Bromine2 回HCID 118221892-(4-chlorophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 7964Chlorobenzene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-eecfa46de4a149aabb45ebe0dcb1230c
出典データセット
uspto-grants-1992_09
特許番号
US05144041

反応ノート

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