Ethyl trifluoroacetate → 1-(4-Chloro-2-fluorophenyl)-2,2,2-trifluoroethan-1-one

HRID 1023142ノート

反応式

HRID 1023142 の反応式
[Li]CCCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10](I)=[C:9]([F:14])[CH:8]=1.[F:15][C:16]([F:23])([F:22])[C:17](OCC)=[O:18]>C1COCC1>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:17](=[O:18])[C:16]([F:23])([F:22])[F:15])=[C:9]([F:14])[CH:8]=1

参加物

5

反応物 3

HCID 9794Ethyl trifluoroacetateHCID 27365624-Chloro-2-fluoro-1-iodobenzeneHCID 178418339Butyllithium

生成物 1

HCID 247268361-(4-Chloro-2-fluorophenyl)-2,2,2-trifluoroethan-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of n-BuLi (1.6 M in hexanes, 4.68 mmol, 2.93 mL) in dry THF was slowly added 4-chloro-2-fluoro-1-iodo-benzene 67h (3.9 mmol, 1.0 g) at −78° C. under N2. The mixture was stirred for 1 h at −78° C. and ethyl trifluoroacetate 67b (0.51 mL, 4.29 mmol) was added. The reaction was allowed to warm to room temperature overnight and was quenched with saturated aqueous NH4Cl solution. The mixture was extracted with EtOAc. The organic extracts were concentrated and purified by flash column chromatography (silica gel, 15% EtOAc/hexanes) to give compound 67i.

後処理

  1. customat −78° C.
  2. temperatureto warm to room temperature overnight
  3. customwas quenched with saturated aqueous NH4Cl solution
  4. extractionThe mixture was extracted with EtOAc
  5. concentrationThe organic extracts were concentrated
  6. custompurified by flash column chromatography (silica gel, 15% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-faaa468eeef145c3bcf580b493226cdd
出典データセット
uspto-grants-2014_05
特許番号
US08722658B2

反応ノート

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