2,2,2-Trifluoroethanol → 5-Bromo-2-(2,2,2-trifluoroethoxy)pyrimidine

HRID 1678065ノート

反応式

HRID 1678065 の反応式
[Br:1][C:2]1[CH:3]=[N:4][C:5](S(C)(=O)=O)=[N:6][CH:7]=1.[CH2:12]([OH:17])[C:13]([F:16])([F:15])[F:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:17][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:6][CH:7]=1

参加物

5

反応物 3

HCID 64092,2,2-TrifluoroethanolHCID 11430Potassium CarbonateHCID 3192865-Bromo-2-(methylsulphonyl)pyrimidine

生成物 1

HCID 179595455-Bromo-2-(2,2,2-trifluoroethoxy)pyrimidine収率 74%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mechanically stirred slurry of 5-bromo-2-(methanesulfonyl)pyrimidine (24 g, 0.10 mol), trifluoroethanol (15 g, 0.15 mol), and potassium carbonate (28 g, 0.20 mol) in acetonitrile (250 mL) was heated at 70° C. for 12 hours. HPLC analysis indicated complete conversion. The solids were removed by filtration, and rinsed well with acetonitrile. The solvent was removed in vacuo and the residue partitioned between ether (50 mL) and water (25 mL). The aqueous phase was extracted with ether (2×25 mL), the organic layers combined, and washed with brine. Dried (Na2SO4), filtered, and solvent removed in vacuo, affording product as a pale yellow liquid, 19 g, 74 percent yield.

後処理

  1. customThe solids were removed by filtration
  2. washrinsed well with acetonitrile
  3. customThe solvent was removed in vacuo
  4. customthe residue partitioned between ether (50 mL) and water (25 mL)
  5. extractionThe aqueous phase was extracted with ether (2×25 mL)
  6. washwashed with brine
  7. dry with materialDried (Na2SO4)
  8. filtrationfiltered
  9. customsolvent removed in vacuo
  10. customaffording product as a pale yellow liquid, 19 g, 74 percent yield

出典と根拠

ORDレコード
ord-e22a2a4566a14d339027b0393de62c10
出典データセット
uspto-grants-2011_08
特許番号
US08008487B2

反応ノート

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