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

HRID 401788

반응식

HRID 401788 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매2회

반응 조건

온도
-5 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-0c640816e0134cb7b4a3840b133f2116
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741934B2

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