Sodium methanethiolate → Pyridine, 5-bromo-2-(methylthio)-3-(trifluoromethyl)-

HRID 1739649노트

반응식

HRID 1739649 반응식
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1.[CH3:13][S-:14].[Na+]>CS(C)=O>[CH3:13][S:14][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1

참가 물질

4

반응물 2

HCID 4378561Sodium methanethiolateHCID 218363025-Bromo-2-chloro-3-(trifluoromethyl)pyridine

생성물 1

HCID 21836291Pyridine, 5-bromo-2-(methylthio)-3-(trifluoromethyl)-수율 67.4%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

The product of Example 6 (3.0 g, 0.012 mol) was dissolved with stirring in dimethyl sulphoxide (30 mL) and sodium methanethiolate (1.2 g, 0.017 mol) was added. The mixture was stirred at room temperature overnight, poured into ice-water, and extracted with hexane (2×50 mL). The organic extracts were combined, washed with water and brine, and dried over anhydrous sodium sulphate. Evaporation of the solvent under reduced pressure and purification of the residue by chromatography over silica (10% ethyl acetate:hexane) gave 2-methylthio-3-trifluoromethyl-5-bromopyridine (2.2 g) as a clear oil.

후처리

  1. extractionextracted with hexane (2×50 mL)
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. customEvaporation of the solvent
  5. customunder reduced pressure and purification of the residue by chromatography over silica (10% ethyl acetate:hexane)

출처 및 근거

ORD 기록
ord-6882abcf675c45eb89ae7cf68e04e503
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968875

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