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Water → 2-(4-Bromo-2-fluorophenyl)oxirane

HRID 2403329
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HRID 2403329 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:11])[CH2:9]Cl)=[C:4]([F:12])[CH:3]=1.[BH4-].[Na+].C[O-].[Na+].O>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][O:11]2)=[C:4]([F:12])[CH:3]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 10942334Sodium MethoxideHCID 790149471-(4-Bromo-2-fluorophenyl)-2-chloroethanone

생성물 1

HCID 627729372-(4-Bromo-2-fluorophenyl)oxirane수율 28.1%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of 1-(4-bromo-2-fluorophenyl)-2-chloroethanone (5.57 g) in ethanol (100 ml) at 5° C. was added portionwise over 5 min NaBH4 (838 mg). The reaction mixture was then stirred at room temperature for 1 hour to afford a light yellow solution. TLC analysis showed the reaction was complete. Sodium methoxide (2.06 ml, 30% solution in methanol) was then added and the reaction mixture was stirred at room temperature overnight. TLC analysis showed the reaction was complete. The reaction mixture was then poured into water and extracted twice with EtOAc. The combined organic layers were washed with saturated brine, then dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel; gradient: 5% to 40% EtOAc in heptane) to afford (RS)-2-(4-bromo-2-fluorophenyl)oxirane (1.35 g, 28%) as a light yellow oil which was used in the next step without further purification. MS (EI): 218 ([{81Br}M]+, 216 ([{79Br}M]+).

후처리

  1. customto afford a light yellow solution
  2. stirringthe reaction mixture was stirred at room temperature overnight
  3. extractionextracted twice with EtOAc
  4. washThe combined organic layers were washed with saturated brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography (silica gel; gradient: 5% to 40% EtOAc in heptane)

출처 및 근거

ORD 기록
ord-82221e7025034942a4958b4be6bff87d
출처 데이터셋
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08802673B2

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