4-Methyl-2-nitroaniline → 2-Bromo-4-methyl-6-nitroaniline

HRID 1781234ノート

反応式

HRID 1781234 の反応式
[Br:1]Br.[CH3:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1>C(O)(=O)C>[Br:1][C:9]1[CH:10]=[C:4]([CH3:3])[CH:5]=[C:6]([N+:11]([O-:13])=[O:12])[C:7]=1[NH2:8]

参加物

4

反応物 2

HCID 69784-Methyl-2-nitroanilineHCID 24408Bromine

生成物 1

HCID 27753062-Bromo-4-methyl-6-nitroaniline収率 98.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

A solution of bromine (23.24 mL, 453.5 mmol) in glacial acetic acid (50 mL) was added dropwise over 2 h to a mechanically-stirred suspension of 4-methyl-2-nitroaniline (60.00 g, 394.3 mmol) in glacial acetic acid (200 mL) at room temperature under a nitrogen atmosphere. The mixture was stirred at room temperature 1 h, and then most of the acetic acid was removed under reduced pressure. The resultant orange solid was dissolved in a mixture of saturated aqueous sodium bicarbonate (1500 mL) and ethyl acetate (500 mL). The layers were separated and the aqueous solution was again extracted with ethyl acetate. The combined organic layers were washed once with water, dried (MgSO4), filtered, and concentrated under reduced pressure to afford the title compound of Step A as an orange solid melting at 64°-65.5° C. (89.694 g, 98%). 1H NMR (CDCl3): δ2.28 (s,3H), 6.45 (br s,2H), 7.55 (s, 1H), 7.94 (s, 1H).

後処理

  1. custommost of the acetic acid was removed under reduced pressure
  2. dissolutionThe resultant orange solid was dissolved in a mixture of saturated aqueous sodium bicarbonate (1500 mL) and ethyl acetate (500 mL)
  3. customThe layers were separated
  4. extractionthe aqueous solution was again extracted with ethyl acetate
  5. washThe combined organic layers were washed once with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-bce3bb869e764396bc23e7298aa8e4ba
出典データセット
uspto-grants-1997_05
特許番号
US05633218

反応ノート

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