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

HRID 600759

반응식

HRID 600759 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 887Methanol용매

반응 조건

온도
-5 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-276d1bfa17f248f19c83fa656aa72423
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902233B2

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