1-Bromo-4-nitrobenzene → 5-Bromo-2-nitroaniline

HRID 252800ノート

反応式

HRID 252800 の反応式
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.Cl.CO[NH2:20]>COCCOC.CN(C)C=O.C(OCC)(=O)C.[Cu]Cl>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([NH2:20])[CH:9]=1

参加物

8

反応物 3

HCID 114661-Bromo-4-nitrobenzeneHCID 521874O-Methylhydroxylamine hydrochlorideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 53147665-Bromo-2-nitroaniline収率 75.2%

試薬・触媒・溶媒 4

HCID 62652Cuprous chloride触媒HCID 6228Dimethylformamide溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of potassium tert-butoxide (14.5 g; 129.2 mmol) and copper(I) chloride (301 mg; 3.04 mmol) in ethyleneglycol dimethylether (120 mL), stirred at 0° C. under nitrogen, a solution of 1-bromo-4-nitro-benzene (1, 6.141 g; 30.4 mmol) and O-methyl-hydroxylamine hydrochloride (3.174 g; 38 mmol) in N,N-dimethylformamide (65 mL) was added drop wise over 103 min, the cooling bath was removed and the mixture was allowed to react at room temperature for 3 h, diluted with ethyl acetate (600 mL) and washed with saturated aqueous ammonium chloride. The organic layer was dried (MgSO4), filtered and concentrated. After purification by flash chromatography (eluent 25% ethyl acetate in hexane), 4.96 g (75% yield) of compound 2 were obtained.

後処理

  1. customthe cooling bath was removed
  2. customto react at room temperature for 3 h
  3. washwashed with saturated aqueous ammonium chloride
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customAfter purification by flash chromatography (eluent 25% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-01c0c8d5cc37496b992f250dde29a32b
出典データセット
uspto-grants-2011_01
特許番号
US07868205B2

反応ノート

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