Trifluoroacetic acid → 1-(1-Azido-1-methylethyl)-3,5-difluorobenzene

HRID 401788

反応式

HRID 401788 の反応式
[NH:1]=[N+:2]=[N-:3].[F:4][C:5]1[CH:6]=[C:7]([C:12](O)([CH3:14])[CH3:13])[CH:8]=[C:9]([F:11])[CH:10]=1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[N:1]([C:12]([C:7]1[CH:8]=[C:9]([F:11])[CH:10]=[C:5]([F:4])[CH:6]=1)([CH3:14])[CH3:13])=[N+:2]=[N-:3]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 24530Hydrazoic acidHCID 577321592-(3,5-Difluorophenyl)propan-2-ol

生成物 1

HCID 577319611-(1-Azido-1-methylethyl)-3,5-difluorobenzene

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

反応条件

温度
-5 °C

実験手順

Hydrogen azide (2M in toluene, 1.5 mol) was added to the solution of 2-(3,5-difluoro-phenyl)-propan-2-ol (Preparation 50, 145 g, 0.84 mol, 1 eq) in chloroform (1 L) and the content of the flask was cooled to −5° C. The mixture of TFA (2.5 mol, 2.98 eq) with chloroform (1:1) was added dropwise at such a rate to keep the internal temperature below −5° C. After the addition was complete, the reaction mixture was allowed to warm to room temperature and stirring was continued for 20 h. The reaction was poured into 2M sodium hydroxide and layers were separated. The aqueous phase was extracted two times with chloroform and combined organic extracts were washed with brine and dried over anhydrous magnesium sulfate. After removal of the solvent, the title compound was used in the next step without further purification (171 g, 0.87 mol, 100%).

後処理

  1. additionwas added dropwise at such a rate
  2. customthe internal temperature below −5° C
  3. additionAfter the addition
  4. temperatureto warm to room temperature
  5. customwere separated
  6. extractionThe aqueous phase was extracted two times with chloroform
  7. washwere washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter removal of the solvent
  10. customthe title compound was used in the next step without further purification (171 g, 0.87 mol, 100%)

出典と根拠

ORDレコード
ord-0c640816e0134cb7b4a3840b133f2116
出典データセット
uspto-grants-2014_06
特許番号
US08741934B2

関連ノート

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