Thionyl Chloride → 5-(Chloromethyl)-2-(trifluoromethyl)pyridine

HRID 512135

반응식

HRID 512135 반응식
S(Cl)([Cl:3])=O.[F:5][C:6]([F:16])([F:15])[C:7]1[N:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=1>C(Cl)Cl>[Cl:3][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]([F:16])([F:15])[F:5])=[N:12][CH:11]=1

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 36138956-(Trifluoromethyl)pyridine-3-methanol

생성물 1

HCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Thionyl chloride (40.3 mL, 554 mmol) was slowly added to a solution of (6-trifluoromethylpyridin-3-yl)-methanol (19.6 g, 111 mmol) in DCM (195 mL) at room temperature under nitrogen. The reaction mixture was stirred at reflux for 16 hours then concentrated under reduced pressure. The residue was dissolved in AcOEt (200 mL), washed with saturated aqueous sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give crude 5-chloromethyl-2-trifluoromethylpyridine as a brown oil which was used in the following step without further purification (19.5 g, 90%). 1H NMR (400 MHz, CDCl3) δ ppm 8.74 (s, 1 H), 7.94 (d, J=8.4 Hz, 1 H), 7.72 (d, J=8.4 Hz 1H), 4.66 (s, 2 H). 19F NMR (400 MHz, CDCl3) δ 168 cm−1. MS m/z 196.15; 198.09

후처리

  1. temperatureat reflux for 16 hours
  2. concentrationthen concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in AcOEt (200 mL)
  4. washwashed with saturated aqueous sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-71b55fac469c45f183426faa2cebeaec
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102591B2

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