Stannous chloride dihydrate → 5-Bromo-2-fluoro-4-methylaniline

HRID 1665774

반응식

HRID 1665774 반응식
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([F:11])=[CH:4][C:3]=1[CH3:12].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C(O)C>[Br:1][C:2]1[C:3]([CH3:12])=[CH:4][C:5]([F:11])=[C:6]([CH:7]=1)[NH2:8]

참가 물질

5

반응물 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 100369831-Bromo-4-fluoro-2-methyl-5-nitrobenzene

생성물 1

HCID 467391145-Bromo-2-fluoro-4-methylaniline수율 31.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of 1-bromo-4-fluoro-2-methyl-5-nitrobenzene (18.0 g) in ethanol (300 mL) was added SnCl2.2H2O (51.8 g, 0.230 mol) at room temperature. The mixture was heated at reflux for 3 h. The solvent was evaporated under reduced pressure to give a residue, which was poured into ice water. The aqueous phase was basified with sat. NaHCO3 to pH 7. The solid was filtered off and the filtrate was extracted with dichloromethane (200 mL×3). The combined organics were dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by column chromatography (petroleum ether/EtOAc=10/1) to afford 5-bromo-2-fluoro-4-methylaniline (5.0 g, 30% yield for two steps). 1H NMR (400 MHz, CDCl3) δ 6.96 (d, J=8.8 Hz, 1 H), 6.86 (d, J=11.6 Hz, 1 H), 3.64 (br, 2 H), 2.26 (s, 3 H). MS (ESI) m/z (M+H+) 204.0.

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. customThe solvent was evaporated under reduced pressure
  4. customto give a residue, which
  5. filtrationThe solid was filtered off
  6. extractionthe filtrate was extracted with dichloromethane (200 mL×3)
  7. dry with materialThe combined organics were dried over anhydrous Na2SO4
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography (petroleum ether/EtOAc=10/1)

출처 및 근거

ORD 기록
ord-938d751751154f9e99a786938790c39a
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039491B2

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