Decylbenzene → 1,4-Dibromo-2,5-bis((4-decylphenyl)carbonyl)benzene

HRID 1166024

반응식

HRID 1166024 반응식
[Br:1][C:2]1[CH:10]=[C:9]([C:11](Cl)=[O:12])[C:8]([Br:14])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].[C:19]1([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[C:9]([C:11]([C:22]2[CH:23]=[CH:24][C:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:20][CH:21]=2)=[O:12])[C:8]([Br:14])=[CH:7][C:3]=1[C:4]([C:22]1[CH:21]=[CH:20][C:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:24][CH:23]=1)=[O:5]

참가 물질

5

반응물 3

HCID 7716DecylbenzeneHCID 6451240Aluminum(III) ChlorideHCID 229969282,5-Dibromobenzene-1,4-dicarbonyl dichloride

생성물 1

HCID 229969271,4-Dibromo-2,5-bis((4-decylphenyl)carbonyl)benzene수율 74.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

Compound 7 (19.2 g, 0.059 mol) was dissolved in 100 mL of dry CH2Cl2, and aluminum chloride (16.6 g, 0.12 mol) was added. The reaction turned orange and some precipitate formed. The reaction was cooled to 0° C., and phenyldecane (45.3 g, 0.21 mol) in 50 mL of dry CH2Cl2 was added through an additional funnel. The reaction was stirred at room temperature under nitrogen overnight. The reaction was quenched carefully with 1 N HCl, extracted with CH2Cl2, and the combined organic phase was dried over MgSO4. The crude product was obtained as off-white solid and was recrystallized from acetone to give 31.8 g of pure product as white crystals at 74% yield. 1H NMR (CDCl3) δ (ppm): 0.88 (t, J=6.7 Hz, 6H), 1.26-1.32 (m, 28H), 1.62-1.67 (m, 4H), 2.69 (t, J=7.6 Hz, 4H), 7.32 (d, J=7.9 Hz, 4H), 7.58 (s, 2H), 7.76 (d, J=7.9 Hz, 4H). Mp 128-129° C.

후처리

  1. customsome precipitate formed
  2. customThe reaction was quenched carefully with 1 N HCl
  3. extractionextracted with CH2Cl2
  4. dry with materialthe combined organic phase was dried over MgSO4
  5. customThe crude product was obtained as off-white solid
  6. customwas recrystallized from acetone

출처 및 근거

ORD 기록
ord-6bb04464ee3a436dbb23605c0d87f182
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613457B2

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