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

HRID 518002Notes

Reaction equation

HRID 518002 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-15a95a9b2c83485b99a7ffd967b1a140
Source dataset
uspto-grants-2015_08
Patent number
US09115126B2

Reaction notes

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