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

HRID 512142

반응식

HRID 512142 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 336979635-Bromo-2-(trifluoromethyl)pyrimidine수율 16.7%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a5e49ed79b414c7f9c2e3af28f397992
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102591B2

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