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

HRID 393614

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HRID 393614 반응식
N([O-])=[O:2].[Na+].[C:5](=[O:18])([O:16][CH3:17])[O:6][C:7]1[CH:12]=[C:11](N)[C:10]([F:14])=[CH:9][C:8]=1[CH3:15]>O.S(=O)(=O)(O)O.O.O.O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O.[Cu]=O>[C:5](=[O:18])([O:16][CH3:17])[O:6][C:7]1[CH:12]=[C:11]([OH:2])[C:10]([F:14])=[CH:9][C:8]=1[CH3:15]

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 dropwise to a solution of (5-amino-4-fluoro-2-methylphenyl) methyl carbonate (3.93 g, 20 mmol) in 35% sulphuric acid (48 ml) at 0° C. The 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) was 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 (4-fluoro-5-hydroxy-2-methylphenyl) methyl carbonate (2.13 g, 53%) as a yellow solid.

후처리

  1. additionwas 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-35fce86474504acf894dc7bb42ac50b5
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809097B1

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