p-Toluenesulfonic acid → 4,4'-Dibromotriphenylamine

HRID 571023

反応式

HRID 571023 の反応式
[CH:1]1[C:6]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=[C:3]([Br:15])[CH:2]=1.[C:16]1(=O)[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:16]1[CH:21]=[CH:20][C:19]([N:7]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)[C:6]2[CH:1]=[CH:2][C:3]([Br:15])=[CH:4][CH:5]=2)=[CH:18][CH:17]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 125111,4-CyclohexanedioneHCID 629950Bis(4-bromophenyl)amine

生成物 1

HCID 135947074,4'-Dibromotriphenylamine収率 67%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

A mixture of 4,4′-dibromodiphenylamine (7.3 g. 22 mmol), cyclohexane-1,4-dione (2.5 g., 23.3 mole), para-toluenesulfonic acid (0.1 g.), and toluene (100 mL) was kept at reflux with a Dean-Stark 15 phase separator containing 4A molecular sieves. After 18 hours at reflux, the reaction was diluted with toluene, and the toluene solution was washed with water, dried, and concentrated. The residue was dissolved in hexanes, and the hexanes solution was then passed through a column of silica gel to afford 4,4′-dibromotriphenylamine as a colorless glass, 5.04 g., 67% yield. Mass Spec (m/z): 401, 403, 405 (M+).

後処理

  1. temperatureat reflux with a Dean-Stark 15 phase separator
  2. temperatureAfter 18 hours at reflux
  3. washthe toluene solution was washed with water
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in hexanes

出典と根拠

ORDレコード
ord-bdf96a7afd554b108fcf9d56789309d2
出典データセット
uspto-grants-2015_05
特許番号
US09024037B1

関連ノート

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