Sodium Carbonate → 9-(3-Bromophenyl)phenanthrene

HRID 1429322ノート

反応式

HRID 1429322 の反応式
[CH:1]1[C:14]2[CH:13]=[C:12](B(O)O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:18][C:19]1[CH:20]=[C:21](I)[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.C(COC)OC>[Br:18][C:19]1[CH:24]=[C:23]([C:12]2[C:11]3[C:6]([C:5]4[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=4[CH:13]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:22]=[CH:21][CH:20]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 117757049-Phenanthracenylboronic acid

生成物 1

HCID 221380359-(3-Bromophenyl)phenanthrene収率 74%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

実験手順

In argon atmosphere, a mixture of 31.4 g (141 mmol) of 9-phenanthreneboronic acid, 40.0 g (141 mmol) of 3-bromoiodobenzene, 3.30 g (2.83 mmol) of tetrakis(triphenylphosphine)palladium (0), 200 ml of toluene, 50 ml of dimethoxyethane and 212 ml of a 2 M sodium carbonate aqueous solution, and the mixture was refluxed under stirring for 4 h. After the reaction, the reaction mixture was added with toluene and washed with water. The organic phase was dried over sodium sulfate, and then toluene was removed by distillation under reduced pressure. The residue was purified by silica gel chromatography to obtain 34.7 g (yield: 74%) of 9-(3-bromophenyl)phenanthrene.

後処理

  1. temperaturethe mixture was refluxed
  2. customAfter the reaction
  3. washwashed with water
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. customtoluene was removed by distillation under reduced pressure
  6. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-515554f0bb124ebc9cdfcbc15dd1be57
出典データセット
uspto-grants-2015_01
特許番号
US08940412B2

反応ノート

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