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Hydrochloric Acid → 2-But-1-enyl-5-(4'-ethyl-2,3-difluorobiphenyl-4-yl)selenophene

HRID 1873438
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HRID 1873438 반응식
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH3:4].[CH2:24]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([C:38]3[Se:42][C:41]([CH:43]=O)=[CH:40][CH:39]=3)=[C:34]([F:45])[C:33]=2[F:46])=[CH:28][CH:27]=1)[CH3:25].CC(C)([O-])C.[K+].Cl>C1COCC1.O>[CH:43]([C:41]1[Se:42][C:38]([C:35]2[CH:36]=[CH:37][C:32]([C:29]3[CH:30]=[CH:31][C:26]([CH2:24][CH3:25])=[CH:27][CH:28]=3)=[C:33]([F:46])[C:34]=2[F:45])=[CH:39][CH:40]=1)=[CH:2][CH2:3][CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 80374Propyltriphenylphosphonium bromideHCID 23665647Potassium tert-butoxideHCID 59456278HCID 59456278, 화합물

생성물 1

HCID 722902622-But-1-enyl-5-(4'-ethyl-2,3-difluorobiphenyl-4-yl)selenophene

시약·촉매·용매 2

HCID 962Water
용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

4.8 g (12.0 mmol) of propyltriphenylphosphonium bromide are initially introduced together with 3.60 g (9.56 mmol) of 5-(4′-ethyl-2,3-difluoro-biphenyl-4-yl)selenophene-2-carbaldehyde in 180 ml of THF, and a solution of 1.30 g (11.6 mmol) of potassium tert-butoxide in 20 ml of THF is added with ice-cooling. The mixture is stirred at RT for 1 h. Water and 2 N hydrochloric acid are added, and the batch is extracted with MTBE. The organic phase is 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, n-heptane:toluene=95:5). 2-But-1-enyl-5-(4′-ethyl-2,3-difluorobiphenyl-4-yl)selenophene is obtained as a yellow solid.

후처리

  1. temperaturecooling
  2. extractionthe batch is extracted with MTBE
  3. washThe organic phase is 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, n-heptane:toluene=95:5)

출처 및 근거

ORD 기록
ord-d2ff46c953834ec5af1911c0be0761b4
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08304036B2

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