Thionyl Chloride → 2,4-Dichloro-5-(chloromethyl)pyridine

HRID 1992649노트

반응식

HRID 1992649 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][C:3]=1[CH2:9]O.S(Cl)([Cl:13])=O>>[Cl:8][C:6]1[CH:7]=[C:2]([Cl:1])[C:3]([CH2:9][Cl:13])=[CH:4][N:5]=1

참가 물질

3

반응물 2

HCID 24386Thionyl ChlorideHCID 2762727(4,6-Dichloropyridin-3-yl)methanol

생성물 1

HCID 27627282,4-Dichloro-5-(chloromethyl)pyridine

실험 절차

(4,6-Dichloro-pyridin-3-yl)-methanol (2.21 g, 12.41 mmol) is cooled under an atmosphere of argon to 0° C. Thionyl chloride (8 ml) is carefully added. After 5 minutes at 0° C., the solution is heated to reflux. After 10 minutes, TLC analysis indicated complete conversion of the starting material. After cooling to RT, excess thionyl chloride is removed via a membrane pump. The remaining oil is dissolved in EtOAc. The solution is poured into a concentrated aqueous solution of NaHCO3. The organic layer is separated and washed twice with a concentrated aqueous solution of NaCl. After drying over Na2SO4, the organic solvent is removed to afford the title compound of adequate purity for immediate further use. 1H NMR (CDCl3, 400 MHz): δ 4.65 (s, 2H), 7.42 (s, 1H), 8.44 (s,1H). ES+−MS: 195, 197, 199 (3 Cl) [M+H]+.

후처리

  1. temperaturethe solution is heated to reflux
  2. waitAfter 10 minutes
  3. customexcess thionyl chloride is removed via a membrane pump
  4. dissolutionThe remaining oil is dissolved in EtOAc
  5. additionThe solution is poured into a concentrated aqueous solution of NaHCO3
  6. customThe organic layer is separated
  7. washwashed twice with a concentrated aqueous solution of NaCl
  8. dry with materialAfter drying over Na2SO4
  9. customthe organic solvent is removed

출처 및 근거

ORD 기록
ord-19b86f8a18ae4a2fae8e7e4290c9e5f6
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07648989B2

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