Sodium Carbonate → 4-Selenophen-2-ylphenol

HRID 1873423

反応式

HRID 1873423 の反応式
I[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.[OH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CC(OC)(C)C.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>[Se:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:11]1[CH:12]=[CH:13][C:8]([OH:7])=[CH:9][CH:10]=1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 1421832-IodoselenopheneHCID 2773454(2-Hydroxyphenyl)boronic acid

生成物 1

HCID 126128064-Selenophen-2-ylphenol

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 15413tert-Butyl methyl ether溶媒HCID 21863594Toluene ethanol溶媒

実験手順

A mixture of 27.9 g (0.11 mol) of 2-iodoselenophene, 15.0 g (0.11 mol) of 2-hydroxyphenylboronic acid, 6.8 g (5.88 mmol) of tetrakis(triphenylphosphine)palladium(0) and 235 ml of 2 N sodium carbonate soln. in 600 ml of toluene/ethanol (1:1) is heated under reflux for 19 h. The mixture is diluted with MTBE and washed with water. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1→1:1). Further purification is carried out by digestion in cold n-heptane; 4-selenophen-2-ylphenol is obtained as a beige solid.

後処理

  1. temperatureunder reflux for 19 h
  2. washwashed with water
  3. extractionThe aqueous phase is extracted with MTBE
  4. washthe combined organic phases are washed with sat. sodium chloride soln
  5. customThe solution is dried
  6. concentrationconcentrated to dryness
  7. customThe residue is purified by column chromatography (SiO2, n-heptane:MTBE=4:1→1:1)
  8. customFurther purification

出典と根拠

ORDレコード
ord-0758f29e362d49169dbb883bb272b792
出典データセット
uspto-grants-2012_11
特許番号
US08304036B2

関連ノート

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