Sulfuric Acid → 3-Bromo-4-(trifluoromethoxy)benzonitrile
Reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1.S(=O)(=O)(O)O.[Br:19]([O-])(=O)=O.[K+]>O>[Br:19][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=1[O:3][C:2]([F:12])([F:13])[F:1])[C:8]#[N:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
4-(Trifluoromethoxy)benzonitrile (5.57 g, 29.8 mmol) was added to 50% aqueous sulfuric acid (60 ml) and the mixture was warmed to 80° C. Potassium bromate (5.97 g, 35.7 mmol) was added in portions over 2 hours and the mixture was stirred at 80° C. for a further 2 hours. The mixture was cooled to room temperature and poured into water (200 ml). The mixture was extracted with ethyl acetate (3×200 ml) and the combined organic layers were dried (MgSO4) and evaporated under reduced pressure to give the title compound as an orange oil (6.0 g) which contained 4-trifluoromethoxy)benzonitrile (ca. 30%) as determined by 1H NMR. 1H NMR (250 MHz, CDCl3) δ 7.97 (1H, d, J=2.0 Hz), 7.68 (1H, dd, J=8.5, 2.0 Hz), and 7.42 (1H, dq, J=8.5, 1.5 Hz).
Workup
- temperatureThe mixture was cooled to room temperature
- extractionThe mixture was extracted with ethyl acetate (3×200 ml)
- dry with materialthe combined organic layers were dried (MgSO4)
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-2d0f47d4f98d439180ec5461e785d0a0
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06060469
Reaction notes
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