Ethyl chloroformate → 2-bromo-4,6-difluoro-N-carbethoxy aniline

HRID 8111

反応式

HRID 8111 の反応式
[Br:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].Cl[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(OCC)(=O)C.CCCCCC>N1C=CC=CC=1>[Br:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH:4][C:12]([O:14][CH2:15][CH3:16])=[O:13]

参加物

5

反応物 3

HCID 10928Ethyl chloroformateHCID 1362852-Bromo-4,6-DifluoroanilineHCID 21226206Ethyl acetate hexane

生成物 1

HCID 170685752-bromo-4,6-difluoro-N-carbethoxy aniline収率 94%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a vigorously stirred solution of 2-bromo-4,6-difluoro aniline (100 g, 0.48 mol) in pyridine (400 mL), at 0° C., is added ethyl chloroformate (70 ml, 0.73 mol) at a rate to keep the temperature below 5° C. When addition is complete, the mixture is stirred at 0° C.–5° C. an additional 2 hours while monitoring by TLC (20% ethyl acetate/hexane, UV). The reaction is then allowed to warm to room temperature, filtered and the filtrate concentrated. The residue is dissolved in diethyl ether/ethyl acetate (500 ml/250 ml) and washed with H2O, 2.5 N HCl, aqueous NaHCO3, brine, dried (Na2SO4), filtered, concentrated, and triturated with petroleum ether to give 126 g of 2-bromo-4,6-difluoro-N-carbethoxy aniline (94%).

後処理

  1. customthe temperature below 5° C
  2. additionWhen addition
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated
  5. dissolutionThe residue is dissolved in diethyl ether/ethyl acetate (500 ml/250 ml)
  6. washwashed with H2O, 2.5 N HCl, aqueous NaHCO3, brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customtriturated with petroleum ether

出典と根拠

ORDレコード
ord-71909e61d7c54e33a7c5b60a56e3b72e
出典データセット
uspto-grants-2006_08
特許番号
US07087635B2

関連ノート

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