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Tetrahydrofuran → 2-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-ethenylbenzonitrile

HRID 474638
ノート
印刷プレビュー

反応式

HRID 474638 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:18]=[CH:17][C:16]([CH:19]=O)=[CH:15][C:12]=2[C:13]#[N:14])=[CH:6][C:5]=1[C:21]([F:24])([F:23])[F:22].[CH2:25]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:18]=[CH:17][C:16]([CH:19]=[CH2:25])=[CH:15][C:12]=2[C:13]#[N:14])=[CH:6][C:5]=1[C:21]([F:24])([F:23])[F:22]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86666201Benzonitrile, 2-[4-chloro-3-(trifluoromethyl)phenoxy]-5-formyl-

生成物 1

HCID 668256152-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}-5-ethenylbenzonitrile収率 36.2%

試薬・触媒・溶媒 1

HCID 74505Methyltriphenyliphosphonium bromide触媒

実験手順

To a solution of NaH (0.798 g, 19.96 mmol) in dry THF (15 mL) was added methyltriphenylphosphonium bromide (7.13 g, 19.96 mmol). The mixture was stirred at room temperature for 0.5 h. Then 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-formylbenzonitrile (5.0 g, 15.35 mmol) was added. Stirring continued for 1.5 h, and the mixture was quenched by ice water. THF was removed by evaporation; the aqueous layer was extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated to afford the title compound (1.8 g, 5.56 mmol, 36.2% yield).

後処理

  1. stirringStirring
  2. waitcontinued for 1.5 h
  3. customthe mixture was quenched by ice water
  4. customTHF was removed by evaporation
  5. extractionthe aqueous layer was extracted with DCM
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-db6c85402d914284a45506163442fd60
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08637536B2

反応ノート

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