Phosphorus oxychloride → 2,6-Dichloro-3-(trifluoromethyl)pyridine

HRID 545082ノート

反応式

HRID 545082 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N+:3]=1[O-].O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:4]1[C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=[C:2]([Cl:1])[N:3]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 154483422-Chloro-5-(trifluoromethyl)pyridine 1-oxide

生成物 1

HCID 18103372,6-Dichloro-3-(trifluoromethyl)pyridine

実験手順

Heat a mixture of 2-chloro-5-trifluoromethylpyridine-N-oxide (40 g, 202.5 mmol) and POCl3 (200 mL) to 80° C. and stir for 16 hours. After cooling to room temperature, remove the excess POCl3 under vacuum. Pour the residue into ice water, and neutralize the mixture to pH=7 with solid NaHCO3. Extract the resulting mixture with diethyl ether (3×80 mL), dry the combined ether extracts (Na2SO4), filter, and evaporate to give a brown oil. Purification by column chromatography affords the title product as pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 1H), 7.41 (d, 1H).

後処理

  1. temperatureHeat
  2. customremove the excess POCl3 under vacuum
  3. additionPour the residue into ice water, and neutralize the mixture to pH=7 with solid NaHCO3
  4. extractionExtract the resulting mixture with diethyl ether (3×80 mL)
  5. dry with materialdry the combined ether
  6. filtrationfilter
  7. customevaporate
  8. customto give a brown oil
  9. customPurification by column chromatography

出典と根拠

ORDレコード
ord-a2bd30138627462f8e3e1a1d7a17ece1
出典データセット
uspto-grants-2011_05
特許番号
US07935702B2

反応ノート

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