Thiophenol → 2-Bromo-6-phenylsulfanylpyridine

HRID 27703

반응식

HRID 27703 반응식
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[N:10]=1>O1CCCC1.CN(C)P(=O)(N(C)C)N(C)C.O>[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:10]=1

참가 물질

6

반응물 2

HCID 7969ThiophenolHCID 122742,6-Dibromopyridine

생성물 1

HCID 8245912-Bromo-6-phenylsulfanylpyridine

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 12679Hexamethylphosphoramide용매3회

실험 절차

To sodium hydride, 0.91 g, (22.3 mmol) (washed with hexane) is added, under nitrogen, 8 ml of tetrahydrofuran. The suspension is then cooled in an ice bath. Thiophenol (2.32 g, 21.1 mmol) in 8 ml of tetrahydrofuran is added dropwise over 30 minutes, after which 4 ml of hexamethylphosphorictriamide is added. The solution is added dropwise over 15 hr to 5 g (21.1 mmol) 2,6-dibromopyridine in 8 ml tetrahydrofuran and 2 ml hexamethylphosphorictriamide at 24°. The reaction mixture is stirred overnight under nitrogen. After addition of 2 ml hexamethylphosphorictriamide, the solution is refluxed for 3 days, then diluted with water and extracted with ether, washed with 5% sodium hydroxide (2×), water (3×) and brine, dried over magnesium sulfate and concentrated. The residue is finally washed with 100 ml cold (ice bath) hexane to give 2-bromo-6-phenylthiopyridine, m.p. 47°.

후처리

  1. washTo sodium hydride, 0.91 g, (22.3 mmol) (washed with hexane)
  2. additionis added, under nitrogen
  3. temperatureThe suspension is then cooled in an ice bath
  4. temperaturethe solution is refluxed for 3 days
  5. extractionextracted with ether
  6. washwashed with 5% sodium hydroxide (2×), water (3×) and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. washThe residue is finally washed with 100 ml cold (ice bath) hexane

출처 및 근거

ORD 기록
ord-75b59b82f4c14b1198acd65eb41b7dfa
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04223033

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