Water → 2-Bromo-5-(2-bromo-acetyl)-benzoic acid methyl ester

HRID 71695

反応式

HRID 71695 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8](I)[CH:7]=[CH:6][C:5]=1[Br:11].C([Sn](CCCC)(CCCC)[CH:18]=[CH:19][O:20]CC)CCC.O.C1C(=O)N([Br:39])C(=O)C1>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([C:19](=[O:20])[CH2:18][Br:39])[CH:7]=[CH:6][C:5]=1[Br:11]

参加物

7

反応物 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)etheneHCID 50998202Methyl 2-bromo-5-iodobenzoate

生成物 1

HCID 596113772-Bromo-5-(2-bromo-acetyl)-benzoic acid methyl ester収率 81.6%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
80 °C

実験手順

To the solution of 2-bromo-5-iodo-benzoic acid methyl ester (4.33 g, 12.7 mmol) and tributyl(ethoxyvinyl)stannane (4.79 g, 13.3 mmol) in dioxane (56 ml) was added PdCl2(PPh3)2 (322 mg). The mixture was heated at 80° C. for 17 hours and was cooled to 0° C. Water (19 ml) was added, followed by slow addition of NBS (2.33 g, 12.9 mmol) over 10 minutes period. The mixture was stirred at 0° C. for additional 40 minutes, and the solvent was removed under reduced pressure. The mixture was diluted with EtOAc, and was washed with water and brine and dried with sodium sulfate. Concentration and purification by flash column chromatography (hexane/EtOAc=2/1) gave 2-bromo-5-(2-bromo-acetyl)-benzoic acid methyl ester (3.48 g).

後処理

  1. temperaturewas cooled to 0° C
  2. customthe solvent was removed under reduced pressure
  3. additionThe mixture was diluted with EtOAc
  4. washwas washed with water and brine
  5. dry with materialdried with sodium sulfate
  6. concentrationConcentration and purification by flash column chromatography (hexane/EtOAc=2/1)

出典と根拠

ORDレコード
ord-fca9257d177c4db48fcc022aeba638b3
出典データセット
uspto-grants-2014_09
特許番号
US08822430B2

関連ノート

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