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

HRID 1166024

反応式

HRID 1166024 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6bb04464ee3a436dbb23605c0d87f182
出典データセット
uspto-grants-2003_09
特許番号
US06613457B2

関連ノート

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