Toluene → 1,3-Bis(triphenylen-2-yl)benzene

HRID 418031

反応式

HRID 418031 の反応式
[CH:1]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.I[C:20]1[CH:25]=[CH:24][CH:23]=[C:22](I)[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[C:33]1([CH3:39])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>O>[CH:4]1[C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[CH:1]=[CH:2][C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:35]2[CH:36]=[CH:37][C:38]3[C:18]4[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=4)[C:6]4[C:39](=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:33]=3[CH:34]=2)[CH:21]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 9170TriphenyleneHCID 11430Potassium CarbonateHCID 12270Benzene, 1,3-diiodo-

生成物 1

HCID 587694461,3-Bis(triphenylen-2-yl)benzene

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
87 °C

実験手順

1.23 g (3.5 mmol) of the triphenylene moronic ester from the previous step, 0.5 g (1.5 mmol) of 1,3-diiodobenzene, 1.0 g (7.5 mmol) of potassium carbonate, 30 mL of toluene, and 10 mL of water was mixed in a 250 mL three-neck flask. The system was purged by nitrogen for 10 min before adding 0.05 g of Pd(PPh3)4. The mixture was then heated up to 87° C. with vigorous stirring. After 24 hr, to the mixture was added 200 mL of methanol. The precipitate was collected by filtration. The solid was washed with copious amount of methanol, then hexanes. The solid was then recrystallized from 80 ml of xylenes. Final purification of the product involved subliming the material at 250° C. 0.35 g product was collected as white needle crystals.

後処理

  1. customThe system was purged by nitrogen for 10 min
  2. additionbefore adding 0.05 g of Pd(PPh3)4
  3. additionto the mixture was added 200 mL of methanol
  4. filtrationThe precipitate was collected by filtration
  5. washThe solid was washed with copious amount of methanol
  6. customThe solid was then recrystallized from 80 ml of xylenes
  7. customFinal purification of the product
  8. customat 250° C
  9. custom0.35 g product was collected as white needle crystals

出典と根拠

ORDレコード
ord-08cdd25534ec478b9be339a85721ed6d
出典データセット
uspto-grants-2012_01
特許番号
US08092924B2

関連ノート

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