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

HRID 393593

반응식

HRID 393593 반응식
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

참가 물질

8

반응물 2

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

생성물 1

HCID 219910495-Benzyloxy-2-fluoro-4-methylphenol수율 27%

시약·촉매·용매 5

HCID 14829Copper oxide촉매HCID 9837674Copper(II) nitrate trihydrate촉매HCID 176Acetic Acid용매HCID 962Water용매2회HCID 1118Sulfuric Acid용매

반응 조건

온도
10 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7113a17c42294fafb4f7216afb6af101
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809097B1

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