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

HRID 393593

反応式

HRID 393593 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

反応条件

温度
10 °C

実験手順

A solution of sodium nitrite (1.68 g, 24 mmol) in water (3.5 ml) was added to a solution of 5-benzyloxy-2-fluoro-4-methylaniline (4.7 g, 20 mmol) in acetic acid (25 ml) and 70% sulphuric acid (25 ml) at 10° C. The mixture was stirred at 10° C. for 20 minutes and a solution of copper(II)nitrate trihydrate (481 g, 2 mol) in water (790 ml) followed by copper(II)oxide (3 g, 19 mmol) was added. The mixture was stirred for 3 hours then extracted with ethyl acetate. The organic layer was washed with water, brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with petroleum ether/ether (85/15) to give 5-benzyloxy-2-fluoro-4-methylphenol (1.25 g, 27%) as an orange oil.

後処理

  1. additionwas added
  2. stirringThe mixture was stirred for 3 hours
  3. extractionthen extracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with petroleum ether/ether (85/15)

出典と根拠

ORDレコード
ord-7113a17c42294fafb4f7216afb6af101
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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