Toluene → 2,7-Diphenyl-9H-carbazole

HRID 1776066

反応式

HRID 1776066 の反応式
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].BrC1[CH:27]=[CH:26][C:25]2[C:24]3[C:19](=[CH:20][C:21](Br)=[CH:22][CH:23]=3)[NH:18][C:17]=2[CH:16]=1.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(O)C>[C:1]1([C:7]2[CH:27]=[CH:26][C:25]3[C:24]4[C:19](=[CH:20][C:21]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:22][CH:23]=4)[NH:18][C:17]=3[CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 111515032,7-Dibromocarbazole

生成物 1

HCID 667173012,7-Diphenyl-9H-carbazole

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Add 80 ml of toluene, 20 ml of ethanol, and 40 g of 2M sodium carbonate aqueous solution to 6.50 g of 2,7-dibromocarbazole, 7.32 g of phenyl boronic acid, 0.734 g of tetrakis triphenyl phosphine palladium; reflux the mixture for three hours while heating in nitrogen atmosphere followed by cooling down to room temperature; filter the mixture to remove insoluble matters; distill away the solvent to obtain 4.15 g of pale bark powder of 2,7-diphenyl carbazole; mix 4.01 g of the thus obtained 2,7-diphenyl carbazole, 4.37 g of 4-(8-hydroxyoctyloxy)iodine benzene, 3.45 g of potassium carbonate, 0.5 g of copper powder, and 20 ml of nitrobenzene; reflux the mixture for seven hours while heating in nitrogen atmosphere followed by cooling down to room temperature; filter the mixture to remove insoluble matters; distill away the solvent; next, refine the resultant with silica gel column chromatography using a liquid mixture of ethyl acetate and hexane as an eluting solution to obtain 2.0 g of a pale bark oily matter of 2.7-diphenyl-N-[4-(8-hydroxyoctyloxyphenyl)]carbazole; and then, tosylate, thioacetylate, and hydrolyze the thus obtained 2.7-diphenyl-N-[4-(8-hydroxyoctyloxyphenyl)]carbazole in the same manner as in Synthesis of Carbazole Derivative 2 to obtain 2,7-diphenyl-N-[4-(8-mercaptooctyloxyphenyl)]carbazole (hereinafter referred to as carbazole derivative 5) having a colorless needle-like crystal represented by the chemical structure 11.

後処理

  1. temperaturereflux the mixture for three hours
  2. temperaturewhile heating in nitrogen atmosphere
  3. filtrationfilter the mixture
  4. customto remove insoluble matters
  5. distillationdistill away the solvent

出典と根拠

ORDレコード
ord-ef9a23af731743a9a3a8b51f0fcb1ddf
出典データセット
uspto-grants-2016_02
特許番号
US09263682B2

関連ノート

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