Potassium Carbonate → 2-(Azidomethyl)-1-methoxy-4-(trifluoromethoxy)benzene

HRID 349248Notes

Reaction equation

HRID 349248 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][C:4]=1[CH2:14]O.S(Cl)(Cl)=O.C(=O)([O-])[O-].[K+].[K+].[N-:26]=[N+:27]=[N-:28].[Na+]>CN(C=O)C.O.CS(C)=O>[N:26]([CH2:14][C:4]1[CH:5]=[C:6]([O:9][C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[N+:27]=[N-:28]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 50112462-Methoxy-5-(trifluoromethoxy)benzyl alcohol

Product 1

HCID 713904042-(Azidomethyl)-1-methoxy-4-(trifluoromethoxy)benzeneYield 96%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dissolve (2-methoxy-5-trifluoromethoxy-phenyl)-methanol (4.49 g, 20.2 mmol) in DMF (40 mL) and treat with thionyl chloride (1.65 g, 22.6 mmol). Stir at RT for 2 h, then treat with potassium carbonate (5.57 g, 40.3 mmol), sodium azide (2.35 g, 36.1 mmol), and DMSO (40 mL). Stir the resulting mixture at RT overnight, then pour into water (100 mL) and extract with ether (3×100 mL). Combine the organic phases and wash with water (2×100 mL) and brine (100 mL). Dry the organic layer (MgSO4), filter, and concentrate to give the title compound (4.77 g, 96%) as a colorless oil that may be used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.14 (m, 2H), 6.87 (m, 1H), 4.34 (s, 2H), 3.85 (s, 3H).

Workup

  1. stirringStir the resulting mixture at RT overnight
  2. extractionextract with ether (3×100 mL)
  3. washCombine the organic phases and wash with water (2×100 mL) and brine (100 mL)
  4. dry with materialDry the organic layer (MgSO4)
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-c15d1c975d884f5181e9f470ccee04b6
Source dataset
uspto-grants-2007_02
Patent number
US07179804B2

Reaction notes

Loading…