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

HRID 393614

反応式

HRID 393614 の反応式
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]

参加物

7

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 14829Copper oxide触媒HCID 9837674Copper(II) nitrate trihydrate触媒HCID 962Water溶媒2 回HCID 1118Sulfuric Acid溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-35fce86474504acf894dc7bb42ac50b5
出典データセット
uspto-grants-2004_10
特許番号
US06809097B1

関連ノート

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