Sodium Carbonate → 4-Selenophen-2-ylphenol

HRID 1873423

반응식

HRID 1873423 반응식
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

참가 물질

7

반응물 3

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

생성물 1

HCID 126128064-Selenophen-2-ylphenol

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 15413tert-Butyl methyl ether용매HCID 21863594Toluene ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0758f29e362d49169dbb883bb272b792
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304036B2

연결된 노트

불러오는 중…