1,3-Dibromobenzene → 2-(3-bromophenyl)-2H-1,2,3-triazole

HRID 881982ノート

反応式

HRID 881982 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[NH:9]1[CH:13]=[CH:12][N:11]=[N:10]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3]>[Br:8][C:4]1[CH:3]=[C:2]([N:10]2[N:11]=[CH:12][CH:13]=[N:9]2)[CH:7]=[CH:6][CH:5]=1.[Br:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[CH:12][N:11]=[N:10]2)[CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 3

HCID 79271,3-DibromobenzeneHCID 10796Cesium carbonateHCID 178418936HCID 178418936、化合物

生成物 2

HCID 124615962-(3-bromophenyl)-2H-1,2,3-triazoleHCID 131061071-(3-Bromophenyl)-1H-1,2,3-triazole

試薬・触媒・溶媒 2

HCID 5483663Ferric acetylacetonate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

To solution of 1,3-dibromobenzene (84 g, 356 mmol) in DMF (700 ml) was added 1,2,3-1H-triazole (30 g, 427 mmol), Cul (6.8 g, 35.6 mmol), Iron(III) acetylacetonate (38 g, 107 mmol) and cesium carbonate (231 g, 712 mmol). The resulting mixture was heated to 120° C. under a nitrogen atmosphere overnight. After cooling to room temperature the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained residue was purified using normal phase chromatography eluting with petroleum ether containing 20% ethyl acetate to give 2-(3-bromophenyl)-2H-1,2,3-triazole (28 g) and 1-(3-bromophenyl)-1H-1,2,3-triazole (11 g) as the pure isomers.

後処理

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe obtained residue was purified
  5. washeluting with petroleum ether containing 20% ethyl acetate

出典と根拠

ORDレコード
ord-b8787cc911c0473398dee315c10e7939
出典データセット
uspto-grants-2015_03
特許番号
US08993757B2

反応ノート

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