Toluene → 2'-Benzyloxy-2-bromobiphenyl

HRID 269534

反応式

HRID 269534 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1B(O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1Br.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>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.O.C(OCC)C.C(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[Br:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

9

反応物 4

HCID 1140TolueneHCID 114141,2-DibromobenzeneHCID 11430Potassium CarbonateHCID 2773253(2-(Benzyloxy)phenyl)boronic acid

生成物 1

HCID 587309892'-Benzyloxy-2-bromobiphenyl収率 69.2%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
90 °C

実験手順

A solution of 2-benzyloxyphenylboronic acid (4.3 g. 19.3 mmol) and 1,2-dibromobenzene (9.11 g, 4.66 ml, 38.6 mmol) in 1:1 toluene:ethanol (150 ml) was stirred under nitrogen and tetrakis(triphenylphosphine)palladium(0) (1.12 g, 0.95 mmol) and potassium carbonate (21.3 g, 154 mmol) added. The reaction was stirred at 90° C. under nitrogen for 2 hours. After cooling, diethyl ether (100 ml) and water (100 ml) were added and the organic phase separated. The aqueous phase was extracted with diethyl ether (50 ml) and the combined organic layers washed with water, dried (MgSO4) and the solvent removed in vacuo. The residue was flash chromatographed (silica gel, 5-15% CH2Cl2-isohexane) to give the title compound as a clear oil (4.53 g, 69%).

後処理

  1. temperatureAfter cooling
  2. customthe organic phase separated
  3. extractionThe aqueous phase was extracted with diethyl ether (50 ml)
  4. washthe combined organic layers washed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo
  7. customchromatographed (silica gel, 5-15% CH2Cl2-isohexane)

出典と根拠

ORDレコード
ord-09e66ee2f0534b5281064bf3de981d67
出典データセット
uspto-grants-2008_11
特許番号
US07446222B2

関連ノート

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