Potassium Fluoride → 5-Bromo-2-(trifluoromethyl)pyrimidine

HRID 512142

反応式

HRID 512142 の反応式
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[Si]([C:13]([F:16])([F:15])[F:14])(C)(C)C.[F-].[K+]>CN(C=O)C.[Cu]I>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:13]([F:16])([F:15])[F:14])=[N:6][CH:7]=1

参加物

6

反応物 3

HCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 70066515-Bromo-2-iodopyrimidine

生成物 1

HCID 336979635-Bromo-2-(trifluoromethyl)pyrimidine収率 16.7%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 5-bromo-2-iodo-pyrimidine (30 g, 0.11 mol), TMSCF3 (30 g, 0.21 mol), KF (9.2 g, 0.16 mol) and CuI (30 g, 0.16 mol) in DMF (300 mL) was stirred at room temperature overnight. The reaction mixture was quenched by NH3.H2O (600 mL) and extracted with EtOAc (500 mL×3). The organic layer was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel (Petroleum ether) to give 5-bromo-2-trifluoromethyl-pyrimidine (4 g, yield: 16.7%). 1H NMR (CDCl3 400 Hz): δ8.90 (s, 2H).

後処理

  1. customThe reaction mixture was quenched by NH3.H2O (600 mL)
  2. extractionextracted with EtOAc (500 mL×3)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (Petroleum ether)

出典と根拠

ORDレコード
ord-a5e49ed79b414c7f9c2e3af28f397992
出典データセット
uspto-grants-2015_08
特許番号
US09102591B2

関連ノート

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