5-Benzyloxy-2-fluoro-4-methylaniline → 5-Benzyloxy-2-fluoro-4-methylphenol

HRID 7495

反応式

HRID 7495 の反応式
N([O-])=[O:2].[Na+].[CH2:5]([O:12][C:13]1[C:14]([CH3:21])=[CH:15][C:16]([F:20])=[C:17]([CH:19]=1)N)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O.C(O)(=O)C.S(=O)(=O)(O)O.O.O.O.[N+]([O-])([O-])=O.[Cu+2].[N+]([O-])([O-])=O.[Cu]=O>[CH2:5]([O:12][C:13]1[C:14]([CH3:21])=[CH:15][C:16]([F:20])=[C:17]([OH:2])[CH:19]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

8

反応物 2

HCID 219910685-Benzyloxy-2-fluoro-4-methylanilineHCID 23668193Sodium Nitrite

生成物 1

HCID 219910495-Benzyloxy-2-fluoro-4-methylphenol収率 27%

試薬・触媒・溶媒 5

HCID 14829Copper oxide触媒HCID 9837674Copper(II) nitrate trihydrate触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回HCID 1118Sulfuric Acid溶媒

実験手順

The starting material 5-benzyloxy-2-fluoro-4-methylphenol, was obtained by adding a solution of sodium nitrite (1.68 g, 24mmol) in water (3.5 ml), dropwise, to a solution of 5-benzyloxy-2-fluoro-4-methylaniline (4.7 g, 20 mmol) in acetic acid (82 ml) and 70% sulphuric acid (3.15 ml) cooled at 10° C. The mixture was stirred vigorously for 20 minutes, then a solution of copper(II)nitrate trihydrate (481 g, 2 mol) in water (790 ml) was added, followed by copper(II)oxide (3 g, 19 mmol). After stirring for 3 hours, the mixture was extracted with ethyl acetate. The organic layer was washed with water and then brine, dried (MgSO4) and the solvent evaporated. The resulting oil was purified by flash chromatography using petroleum ether/ether (85/15) as eluent to give 5-benzyloxy-2-fluoro-4-methylphenol as an orange oil (1.25 g, 27%).

後処理

  1. stirringAfter stirring for 3 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialbrine, dried (MgSO4)
  5. customthe solvent evaporated
  6. customThe resulting oil was purified by flash chromatography

出典と根拠

ORDレコード
ord-051c546095a445e08c053b9eb100de40
出典データセット
uspto-grants-2006_08
特許番号
US07087602B2

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