Ammonium Chloride → HCID 67002199、化合物

HRID 558440ノート

反応式

HRID 558440 の反応式
[F:1][C:2]([F:20])([F:19])[O:3][C:4]1[CH:18]=[CH:17][C:7]([CH2:8]P(=O)(OCC)OCC)=[CH:6][CH:5]=1.[Br:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][C:23]=1[CH:30]=O.CC(C)([O-])C.[K+].[Cl-].[NH4+]>CN(C=O)C.O>[Br:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][C:23]=1[CH:30]=[CH:8][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:19])[F:20])=[CH:18][CH:17]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 225749024-Bromo-3-formylbenzonitrileHCID 23665647Potassium tert-butoxideHCID 57744084HCID 57744084、化合物

生成物 1

HCID 67002199HCID 67002199、化合物収率 44.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
-25 °C

実験手順

Diethyl (4-trifluoromethoxybenzyl)phosphonate (7.8 g) was dissolved in 100 mL of DMF, 5.0 g of 4-bromo-3-formyl-benzonitrile was added, and the mixture was cooled to −25° C. Potassium tert-butoxide (6.4 g) was added, and the mixture was stirred for 2 hours at −25° C. To the reaction mixture, 100 mL of a saturated aqueous solution of ammonium chloride and 100 mL of water were added, and the mixture was extracted 3 times with ethyl acetate (100 mL). The respective organic layers were combined, whereafter the combined organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. The magnesium sulfate was separated by filtration, and the filtrate was concentrated under reduced pressure. The residue was subjected to 100 g silica gel column chromatography to obtain 3.9 g of 4-bromo-3-[2-(4-trifluoromethoxy-phenyl)-vinyl]-benzonitrile as a crude product with the use of an eluant (ethyl acetate and n-hexane, 1:10).

後処理

  1. extractionthe mixture was extracted 3 times with ethyl acetate (100 mL)
  2. washwas washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  4. customThe magnesium sulfate was separated by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-ce0b6dcb9db348808ff8964fbd904482
出典データセット
uspto-grants-2011_11
特許番号
US08063046B2

反応ノート

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