Sodium Azide → 1-(Azidomethyl)-2-(trifluoromethyl)benzene

HRID 1898295Notes

Reaction equation

HRID 1898295 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]([F:12])([F:11])[F:10].[N-:13]=[N+:14]=[N-:15].[Na+]>CS(C)=O>[F:10][C:9]([F:12])([F:11])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:2][N:13]=[N+:14]=[N-:15]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzene

Product 1

HCID 161117391-(Azidomethyl)-2-(trifluoromethyl)benzeneYield 956%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 1-(bromomethyl)-2-(trifluoromethyl)benzene (0.250 g, 0.104 mmol) in DMSO (3.0 mL) was added sodium azide (0.101 g, 0.156 mmol). The reaction mixture was stirred at RT for 3-4 h. The reaction mixture was quenched in water and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated to afford 0.200 g of the desired product. 1HNMR (DMSO-d6): δ 4.63 (s, 2H), 7.60 (d, J=7.8 Hz, 1H), 7.70-7.80 (m, 3H).

Workup

  1. customThe reaction mixture was quenched in water
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1f4be7e3c8514d8f92795bb1cf3181dd
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

Loading…