Water → 4-bromo-2-tert-butylphenylamine

HRID 534821ノート

反応式

HRID 534821 の反応式
[C:1]([C:5]1[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=1[NH2:7])([CH3:4])([CH3:3])[CH3:2].[Br-:12].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[Br:12][C:10]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:11]=1

参加物

5

反応物 3

HCID 962WaterHCID 805742-tert-ButylanilineHCID 23500184Tetra-n-butylammonium tribromide

生成物 1

HCID 119590004-bromo-2-tert-butylphenylamine収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-tert-butylaniline (50 g, 335 mmol) in THF (500 mL) was added tetrabutylammonium tribromide (234.5 g, 335 mmol) at 0° C. After the solution was stirred for 30 minutes at that temperature, it was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated Na2S2O3 solution and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the crude product. The product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=100:0 to 20:80) to provide 4-bromo-2-tert-butylaniline (74.6 g, 98%) as a pink oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated Na2S2O3 solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give the crude product
  6. customThe product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=100:0 to 20:80)

出典と根拠

ORDレコード
ord-579d8ff537f9416b9e7a45def59d3e5e
出典データセット
uspto-grants-2014_10
特許番号
US08853215B2

反応ノート

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