Trifluoroacetic acid → 1-(1-Azidocyclohexyl)-3-(methyloxy)benzene

HRID 852630Notes

Reaction equation

HRID 852630 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2(O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[N-:16]=[N+:17]=[N-:18].[Na+].C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:16]([C:9]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[N+:17]=[N-:18]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 33557Sodium AzideHCID 146851021-(3-Methoxyphenyl)cyclohexan-1-ol

Product 1

HCID 866028821-(1-Azidocyclohexyl)-3-(methyloxy)benzeneYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-[3-(methyloxy)phenyl]cyclohexanol (2.93 g, 14.22 mmol, 1 equiv) in CH2Cl2 (25 ml) under nitrogen at 0° C. was added sodium azide (1.85 g, 28.44 mmol, 2 equiv) then TFA (4.4 ml, 56.89 mmol, 4 equiv) slowly. 40 Ml of CH2Cl2 were then added and the resulting suspension was stirred at room temperature for 16 h then partitioned between Et2O and H2O. The two layers were separated and the organic phase was washed with H2O and a 1N aqueous NaOH solution then dried over MgSO4 and concentrated in vacuo to give 1-(1-azidocyclohexyl)-3-(methyloxy)benzene (D315) (2.78 g, 85%) as a clear oil which was used in the next step without further purification.

Workup

  1. customthen partitioned between Et2O and H2O
  2. customThe two layers were separated
  3. washthe organic phase was washed with H2O
  4. dry with materiala 1N aqueous NaOH solution then dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-430f9fc6d2df4f5eb184b1b09d963e36
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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