Hydrochloric Acid → 2-(2',3'-Difluoro-4'-propoxybiphenyl-4-yl)-5-vinylselenophene

HRID 1873414노트

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HRID 1873414 반응식
[CH3:1]C(C)([O-])C.[K+].[F:7][C:8]1[C:13]([F:14])=[C:12]([O:15][CH2:16][CH2:17][CH3:18])[CH:11]=[CH:10][C:9]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]2[Se:29][C:28]([CH:30]=O)=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.O.Cl>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[F:7][C:8]1[C:13]([F:14])=[C:12]([O:15][CH2:16][CH2:17][CH3:18])[CH:11]=[CH:10][C:9]=1[C:19]1[CH:20]=[CH:21][C:22]([C:25]2[Se:29][C:28]([CH:30]=[CH2:1])=[CH:27][CH:26]=2)=[CH:23][CH:24]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 594563315-(2',3'-Difluoro-4'-propoxybiphenyl-4-yl)selenophene-2-carbaldehyde

생성물 1

HCID 594562742-(2',3'-Difluoro-4'-propoxybiphenyl-4-yl)-5-vinylselenophene

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

4.50 g (12.6 mmol) of methyltriphenylphosphonium bromide are initially introduced in 50 ml of THF at 0° C., and 1.40 g (12.5 mmol) of potassium tert-butoxide dissolved in 30 ml of THF are added. After 1 h, 4.1 g (10.1 mmol) of 5-(2′,3′-difluoro-4′-propoxybiphenyl-4-yl)selenophene-2-carbaldehyde in 100 ml of THF are added, and the batch is stirred at RT for 17 h. Water and 2 N hydrochloric acid are added to the mixture, and the batch is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, toluene). 2-(2′,3′-Difluoro-4′-propoxy-biphenyl-4-yl)-5-vinylselenophene is obtained as an orange solid.

후처리

  1. additionare added
  2. extractionthe batch is extracted with MTBE
  3. washThe combined organic phases are washed with sat. sodium chloride soln
  4. customand dried
  5. concentrationThe solution is concentrated to dryness
  6. customthe residue is purified by column chromatography (SiO2, toluene)

출처 및 근거

ORD 기록
ord-3d76c8498a4d4be59f8eeaabd3b02d0b
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304036B2

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