Acetone → 9-Bromo-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester

HRID 575050

반응식

HRID 575050 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2[C:8](Br)(Br)[CH2:9][O:10][C:11]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:12]=3[C:13]=2[N:14]=1)=[O:4].CC(C)=[O:24]>O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]2[C:8](=[O:24])[CH2:9][O:10][C:11]3[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:12]=3[C:13]=2[N:14]=1)=[O:4]

참가 물질

4

반응물 2

HCID 180AcetoneHCID 866930864,4,9-Tribromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester

생성물 1

HCID 866930859-Bromo-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester수율 86%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

The mixture of 4,4,9-Tribromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (9.0 g, 18.07 mmol) in acetone (250 mL) and water (250 mL) was stirred at room temperature for 4 h. Then the mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (2×200 mL). The combined organic layers were washed with brine, dried over Na2SO4, concentrated to afford the crude product which was triturated with EtOAc and hexane (EtOAc/hexane=1/5). After filtration, the solid was dried in vacuo to afford compound 9-Bromo-4-oxo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid methyl ester (5.5 g, 86%) as a light yellow solid.

후처리

  1. customThen the mixture was partitioned between EtOAc and H2O
  2. extractionThe aqueous layer was extracted with EtOAc (2×200 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto afford the crude product which
  7. customwas triturated with EtOAc and hexane (EtOAc/hexane=1/5)
  8. filtrationAfter filtration
  9. customthe solid was dried in vacuo

출처 및 근거

ORD 기록
ord-1fde194404a645fa8a9a098b5bdb15d2
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034866B2

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