Acetic Acid → 2,3-Dichloro-5-(chloromethyl)pyridine

HRID 600759

反応式

HRID 600759 の反応式
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9](Cl)(Cl)[Cl:10])=[CH:4][N:3]=1.C(O)(=O)C>[Zn].CO>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([CH2:9][Cl:10])=[CH:4][N:3]=1

参加物

5

反応物 2

HCID 176Acetic AcidHCID 946472,3-Dichloro-5-(trichloromethyl)pyridine

生成物 1

HCID 101765362,3-Dichloro-5-(chloromethyl)pyridine

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒

反応条件

温度
-5 °C

実験手順

2,3-dichloro-5-trichloromethylpyridine (36.60 g, 0.139 mol) was added to a flask containing acetic acid (53.50 g, 0.892 mol) and methanol (200 mL). The mixture was cooled to −5° C., and zinc dust (20.01 g, 0.308 mol) was added in small portions at 10 minute intervals. The mixture was stirred mechanically for 4 hours, filtered, and concentrated in vacuo. The residue was dissolved in dichloromethane and washed with brine, followed by saturated aqueous sodium bicarbonate, followed by a second brine wash. The organic phase was dried over magnesium sulfate and concentrated in vacuo to yield 21.55 g (79%) of Preparatory Compound P, 2,3-dichloro-5-(chloromethyl)pyridine, as a yellow liquid (about 65% purity). 1H NMR δ 8.31 (d, 1H, J=2.3 Hz), 7.85 (q, 1H, J=0.4 Hz and J=2.2 Hz), 4.56 (s, 2H). MS (ESI) m/z 199 ([M+4]+, 8), 197 ([M+2]+, 27), 195 ([M]+, 28), 164 (11), 162 (66), 160 (100), 124 (19)

後処理

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with brine
  5. washwash
  6. dry with materialThe organic phase was dried over magnesium sulfate
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-276d1bfa17f248f19c83fa656aa72423
出典データセット
uspto-grants-2011_03
特許番号
US07902233B2

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