Triethyl phosphite → 5-Bromo-6-chlorobenzo[c][1,2,5]oxadiazole

HRID 1468967노트

반응식

HRID 1468967 반응식
[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]2[C:6]([CH:11]=1)=[N+:7]([O-])[O:8][N:9]=2.P(OCC)(OCC)OCC>C(O)C>[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]2=[N:9][O:8][N:7]=[C:6]2[CH:11]=1

참가 물질

4

반응물 2

HCID 31215Triethyl phosphiteHCID 674650696-Bromo-5-chlorobenzo[c][1,2,5]oxadiazole 1-oxide

생성물 1

HCID 674684685-Bromo-6-chlorobenzo[c][1,2,5]oxadiazole수율 79%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

6-Bromo-5-chlorobenzo[c][1,2,5]oxadiazole 1-oxide (4.8 g, 19 mmol) was taken up 150 ml ethanol, heated to reflux, treated with triethyl phosphite (8.8 g, 53 mmol) and heated for 3.5 h. After cooling, the volatiles were removed by rotary evaporation, the residue was taken up in 100 mL dichloromethane and stirred with 50 mL bleach solution for 30 min. The organic phase was washed with 20 mL saturated NaCl, dried (Na2SO4) and evaporated. The crude material was purified by flash chromatography with a 0-30% ethyl acetate-hexane gradient to give the title compound as an orange solid (3.5 g, 79%): mp 68-69° C.; 1H NMR (400 MHz, CDCl3) δ 8.30 (s, 1H), 8.05 (s, 1H); EIMS m/z 232.

후처리

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureheated for 3.5 h
  4. temperatureAfter cooling
  5. customthe volatiles were removed by rotary evaporation
  6. washThe organic phase was washed with 20 mL saturated NaCl
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe crude material was purified by flash chromatography with a 0-30% ethyl acetate-hexane gradient

출처 및 근거

ORD 기록
ord-dd4ba333b7224aa28c5526d6bbc0aadb
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006250B2

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