5-Amino-4-fluoro-2-methylphenyl Methoxyformate → (4-Fluoro-5-hydroxy-2-methylphenyl) methyl carbonate

HRID 279538

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HRID 279538 반응식
N([O-])=[O:2].[Na+].[F:5][C:6]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][C:7]=1N>O.S(=O)(=O)(O)O.O.O.O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O.[Cu]=O>[F:5][C:6]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][C:15]([O:17][CH3:18])=[O:16])=[CH:9][C:7]=1[OH:2]

참가 물질

7

반응물 2

HCID 226250465-Amino-4-fluoro-2-methylphenyl MethoxyformateHCID 23668193Sodium Nitrite

생성물 1

HCID 22625031(4-Fluoro-5-hydroxy-2-methylphenyl) methyl carbonate수율 53.2%

시약·촉매·용매 4

HCID 14829Copper oxide촉매HCID 9837674Copper(II) nitrate trihydrate촉매HCID 962Water용매2회HCID 1118Sulfuric Acid용매

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온도
0 °C

실험 절차

A solution of sodium nitrite (1.63 g, 23 mmol) in water (19 ml) and ice (48 g) was added dropwsie to a solution of 2-fluoro-5-methoxycarbonyloxy-4-methylaniline (3.93 g, 20 mmol) in 35% sulphuric acid (48 ml) at 0° C. The reaction mixture was stirred at 0° C. for 30 minutes and a solution of copper(II)nitrate trihydrate (467 g, 1.93 mol) in water (780 ml) followed by copper(II)oxide (2.65 g, 18 mmol) were added. The solution was extracted with ethyl acetate, the organic layer was washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with petroleum ether/ethyl acetate (8/2) to give 2-fluoro-5-methoxycarbonyloxy-4-methylphenol (2.13 g, 53%) as a yellow solid.

후처리

  1. additionwere added
  2. extractionThe solution was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with petroleum ether/ethyl acetate (8/2)

출처 및 근거

ORD 기록
ord-e70dd8e5684847159b21a5e6e481d2f3
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06362336B1

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