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Potassium Carbonate → tert-Butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoate

HRID 1525660
ノート
印刷プレビュー

反応式

HRID 1525660 の反応式
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:20]=[C:19](F)[C:18]([F:22])=[CH:17][C:9]=1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].[Cl:23][C:24]1[CH:25]=[C:26]([CH2:31][OH:32])[CH:27]=[N:28][C:29]=1[Cl:30]>CS(C)=O>[Cl:23][C:24]1[CH:25]=[C:26]([CH2:31][O:32][C:19]2[C:18]([F:22])=[CH:17][C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[C:8]([F:7])[CH:20]=2)[CH:27]=[N:28][C:29]=1[Cl:30]
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 11430Potassium CarbonateHCID 10868153Tert-butyl 2,4,5-trifluorobenzoateHCID 21882961(5,6-Dichloropyridin-3-yl)methanol

生成物 1

HCID 86682568tert-Butyl 4-((5,6-dichloropyridin-3-yl)methoxy)-2,5-difluorobenzoate収率 97.3%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Potassium carbonate (535 mg, 3.88 mmol) was added to a solution of tert-butyl 2,4,5-trifluorobenzoate (Preparation 10, 275 mg, 1.29 mmol) and (5,6-dichloropyridin-3-yl)methanol (241 mg, 1.36 mmol) in DMSO (5 mL). The reaction mixture was stirred at RT for 18 hours. After cooling the reaction mixture was quenched with water (25 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with water (2×100 mL) and dried over MgSO4, filtered and concentrated in vacuo to give 490 mg of the title compound in a quantitative yield. The crude compound was used without further purification.

後処理

  1. temperatureAfter cooling the reaction mixture
  2. customwas quenched with water (25 mL)
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layers were washed with water (2×100 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d3e8d395c6704a84a1ba36f479fed947
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09085517B2

反応ノート

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