Dichloromethane → 1-Methylpyrene

HRID 1914409ノート

反応式

HRID 1914409 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][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[CH3:18]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O.CN(C)C=O>[CH3:18][C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 1596271-BromopyreneHCID 574072Trimethylboroxine

生成物 1

HCID 169321-Methylpyrene収率 81.7%

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

A mixed solution of 7 g of 1-bromopyrene, 6 g of trimethylboroxin, 12 g of cesium carbonate, 2 g of PdCl2(dppf).CH2Cl2, 80 ml of dimethylformamide and 8 ml of distilled water was heated and stirred under a nitrogen gas stream at 80° C. for 7 hours. The solution was cooled to room temperature and 50 ml of water was poured into the solution, followed by filtration. The resulting solid was purified by silica gel column chromatography and then vacuum-dried to obtain 4.4 g of 1-methylpyrene.

後処理

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfollowed by filtration
  3. customThe resulting solid was purified by silica gel column chromatography
  4. customvacuum-dried

出典と根拠

ORDレコード
ord-fff84b02595d430f86599072f696d4b5
出典データセット
uspto-grants-2013_12
特許番号
US08610345B2

反応ノート

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