Sodium Iodide → 6-bromo-8-ethoxy-4H-benzo[1,3]dioxine

HRID 2079153

반응식

HRID 2079153 반응식
FC(F)(F)[C:3]([OH:5])=[O:4].C(C1C=CC(N[CH:18]([C:34]2[CH:39]=[C:38]([O:40][CH3:41])[C:37](OC)=C[C:35]=2F)C2NC(=O)N(C3C=CC=CC=3C(O)=O)N=2)=CC=1)(=N)N.[H-].[Na+].[Br:47][CH2:48]Cl.[I-].[Na+].[Cl-].[NH4+].[CH3:54]N(C=O)C>C(OCC)(=O)C>[Br:47][C:48]1[CH:37]=[C:38]([O:40][CH2:41][CH3:54])[C:39]2[O:5][CH2:3][O:4][CH2:18][C:34]=2[CH:35]=1

참가 물질

8

반응물 6

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 6333BromochloromethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 1363370832-{3-[(4-carbamimidoylphenylamino)-(2-fluoro-4,5-dimethoxyphenyl)methyl]5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}benzoic Acid Trifluoroacetate

생성물 1

HCID 670968006-bromo-8-ethoxy-4H-benzo[1,3]dioxine

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of this compound in 40 ml of DMF there was added 1g of sodium hydride (60% oily suspension) while cooling on ice, and the mixture was stirred at room temperature for 30 minutes. After then adding 1 ml of bromochloromethane and 0.25 g of sodium iodide to the reaction mixture, it was stirred at 80° C. for 6 hours under a hydrogen atmosphere. Saturated aqueous ammonium chloride was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give 6-bromo-8-ethoxy-4H-benzo[1,3]dioxine (1.62 g).

후처리

  1. temperaturewhile cooling on ice
  2. stirringwas stirred at 80° C. for 6 hours under a hydrogen atmosphere
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationThe desiccating agent was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

출처 및 근거

ORD 기록
ord-035d2348da454e09b4cd0f7fbaefe427
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928228B2

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