Toluene → 1,6-Diphenylpyrene

HRID 1012907ノート

反応式

HRID 1012907 の反応式
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[C:19]1(B(O)O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:34]1(C)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O>[C:19]1([C:2]2[C:15]3[C:16]4=[C:17]5[C:12](=[CH:13][CH:14]=3)[CH:11]=[CH:10][C:9]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[C:8]5[CH:7]=[CH:6][C:5]4=[CH:4][CH:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 176470Pyrene, 1,6-Dibromo-

生成物 1

HCID 591334031,6-Diphenylpyrene収率 99%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
100 °C

実験手順

In a stream of argon, 20 g (55.6 mmol) of 1,6-dibromopyrene, 16.3 g (133 mmol) of phenyl boronic acid, 2.5 g (4 mol %) of tetrakistriphenylphosphine palladium, an aqueous solution containing 26.5 g (65 mmol) of sodium carbonate in 125 mL of water, and 250 mL of toluene were added to a 1-L three-necked flask equipped with a cooling pipe, and the whole was refluxed under heat at 100° C. for 8 hours. After the completion of the reaction, 50 mL of water was added and then a crystal was filtered out, washed with 50 mL of water, 100 mL of ethanol, and 100 mL of toluene. As a result, 15.3 g of 1,6-diphenylpyrene (a white powder) was obtained (99% yield).

後処理

  1. additionwere added to a 1-L three-necked flask
  2. customequipped with a cooling pipe
  3. temperaturethe whole was refluxed
  4. additionwas added
  5. filtrationa crystal was filtered out
  6. washwashed with 50 mL of water, 100 mL of ethanol, and 100 mL of toluene

出典と根拠

ORDレコード
ord-d37b9a12e8084b1fbfd2a2000a4239d7
出典データセット
uspto-grants-2011_07
特許番号
US07981523B2

反応ノート

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