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

HRID 1873416ノート

反応式

HRID 1873416 の反応式
[CH3:1][C:2](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)C.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]=[CH:1][CH3:2])=[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 722902632-(2',3'-Difluoro-4'-propoxybiphenyl-4-yl)-5-propenylselenophene

試薬・触媒・溶媒 2

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

4.70 g (12.5 mmol) of ethyltriphenylphosphonium 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, 4.2 g (10.4 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 18 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′-propoxybiphenyl-4-yl)-5-propenylselenophene 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-8de603f0432b420795973f529e739fde
出典データセット
uspto-grants-2012_11
特許番号
US08304036B2

反応ノート

読み込み中…