Phosphorus oxychloride → 3-Bromo-7-chloro-2-methylthieno[2,3-c]pyridine

HRID 1668968노트

반응식

HRID 1668968 반응식
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][N+:7]([O-])=[CH:8][CH:9]=2)[S:4][C:3]=1[CH3:12].P(Cl)(Cl)([Cl:15])=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[C:10]2[C:5](=[C:6]([Cl:15])[N:7]=[CH:8][CH:9]=2)[S:4][C:3]=1[CH3:12]

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 673397463-bromo-2-methylthieno[2,3-c]pyridine-N-Oxide

생성물 1

HCID 584664573-Bromo-7-chloro-2-methylthieno[2,3-c]pyridine

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
70 °C

실험 절차

3-Bromo-2-methylthieno[2,3-c]pyridine-N-Oxide (0.500 g, 2.05 mmol) was dissolved in chloroform (10 mL) and treated with phosphorous oxychloride (0.955 ml, 10.2 mmol). The reaction was heated to 70° C. while stirring. After 3 hours, the volatiles were removed in vacuo and the residual phosphorous oxychloride was azeotroped with toluene. The resulting residue was taken up in DCM and washed (2×) with an aqueous saturated solution of sodium bicarbonate, then with water and then brine. The organic layer was then dried with sodium sulfate and purified by column chromatography on silica gel using a gradient of 20-60% EtOAc in hexanes to give 3-bromo-7-chloro-2-methylthieno[2,3-c]pyridine as a yellow solid. MS (M+H)+ 263.

후처리

  1. customthe volatiles were removed in vacuo
  2. customthe residual phosphorous oxychloride was azeotroped with toluene
  3. washwashed (2×) with an aqueous saturated solution of sodium bicarbonate
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. custompurified by column chromatography on silica gel using a gradient of 20-60% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-904f2d12124047e0becc5206b44233b4
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989461B2

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