Sulfuric Acid → 3-Bromo-5-nitrophenol

HRID 447051ノート

反応式

HRID 447051 の反応式
N[C:2]1[C:7]([Br:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[OH:12].OS(O)(=O)=O.N([O-])=O.[Na+]>CCO.O>[Br:8][C:7]1[CH:2]=[C:3]([OH:12])[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[CH:6]=1

参加物

6

反応物 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 49766558HCID 49766558、化合物

生成物 1

HCID 104889843-Bromo-5-nitrophenol収率 82.2%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

To an ice-cold solution of 2-amino-3-bromo-5-nitro-phenol (6.50 g, 27.89 mmol) in EtOH (150.0 mL) was added concentrated H2SO4 (9.40 mL, 177.13 mmol) portion wise. The reaction mixture was then heated to 50° C. followed by portion wise addition of NaNO2 (6.19 g, 89.82 mmol). The resulting solution was refluxed at 80° C. for 2 h. The reaction mixture was then diluted with water and extracted with EtOAc (3×150.0 mL). The combined organics was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude was purified over silica gel (100-200 M, 10% EtOAc-Hexane) to get the desired product (5.0 g, 82%).

後処理

  1. temperatureThe resulting solution was refluxed at 80° C. for 2 h
  2. extractionextracted with EtOAc (3×150.0 mL)
  3. dry with materialThe combined organics was dried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified over silica gel (100-200 M, 10% EtOAc-Hexane)

出典と根拠

ORDレコード
ord-135bcce3e9a943739d533a5f5f2e9b2a
出典データセット
uspto-grants-2013_07
特許番号
US08481544B2

反応ノート

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