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

HRID 1873414ノート

反応式

HRID 1873414 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3d76c8498a4d4be59f8eeaabd3b02d0b
出典データセット
uspto-grants-2012_11
特許番号
US08304036B2

反応ノート

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