p-Toluenesulfonic acid → 4,4'-Dibromotriphenylamine

HRID 380187

반응식

HRID 380187 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 135947074,4'-Dibromotriphenylamine수율 67%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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 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 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+).

후처리

  1. temperatureat reflux with a Dean-Stark 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

출처 및 근거

ORD 기록
ord-0e8572c34d9844d4b11a879b2e72e1fe
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300502B1

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