Water → 1-(2-Azidoethoxy)-4-bromo-2-(trifluoromethyl)benzene

HRID 518002노트

반응식

HRID 518002 반응식
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[C:16]([F:19])([F:18])[F:17])(=O)=O.C(=O)([O-])[O-].[K+].[K+].[N-:26]=[N+:27]=[N-:28].[Na+].O>CN(C=O)C.CCOC(C)=O>[N:26]([CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[C:16]([F:19])([F:18])[F:17])=[N+:27]=[N-:28]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 33557Sodium AzideHCID 866733562-(4-Bromo-2-(trifluoromethyl)phenoxy)ethyl methanesulfonate

생성물 1

HCID 866733571-(2-Azidoethoxy)-4-bromo-2-(trifluoromethyl)benzene

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

2-(4-Bromo-2-(trifluoromethyl)phenoxy)ethyl methanesulfonate (15.54 mmol, 5.643 g) and potassium carbonate (46.6 mmol, 6.44 g) were combined and stirred in DMF (50 ml). Sodium azide (46.6 mmol, 3.03 g) was added and the reaction stirred at room temperature overnight. Starting material remained. Reaction was heated to 60° C. for 5 hours. The reaction mixture was poured into water and diluted with EtOAc. The layers were separated and the organic dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by silica chromatography, eluting with a gradient of heptane—50/50 heptane/EtOAc to afford 1-(2-azidoethoxy)-4-bromo-2-(trifluoromethyl)benzene. (2.27 g)

후처리

  1. customReaction
  2. temperaturewas heated to 60° C. for 5 hours
  3. customThe layers were separated
  4. dry with materialthe organic dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica chromatography
  7. washeluting with a gradient of heptane—50/50 heptane/EtOAc

출처 및 근거

ORD 기록
ord-15a95a9b2c83485b99a7ffd967b1a140
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115126B2

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