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

HRID 7495

반응식

HRID 7495 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

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-051c546095a445e08c053b9eb100de40
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087602B2

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