Sulfuric Acid → 4-[3-Bromo-4-(trifluoromethoxy)phenyl]pyridine

HRID 1107289Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1.S(=O)(=O)(O)O.[Br:23]([O-])(=O)=O.[K+].[OH-].[Na+]>O>[Br:23][C:9]1[CH:8]=[C:7]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]=1[O:3][C:2]([F:1])([F:16])[F:17]

Participants

Conditions

Temperature: 80 °C

Procedure

4-[4-(Trifluoromethoxy)phenyl]pyridine (500 mg, 2.1 mmol) was suspended in water (2 ml) and conc. sulphuric acid (2 ml). The suspension was heated to 80° C. and potassium bromate (386 mg, 2.31 mmol) was added in portions over 2 hours. The reaction was stirred at 80° C. for a further 2 hours, allowed to cool to ambient temperature and then poured onto ice. The solution was basified with 4N sodium hydroxide solution, extracted with ethyl acetate (2×30 ml) and the combined organic layers were washed with water. The solution was dried over sodium sulphate and the solvent was removed in vacuo giving an oil (467 mg) which was used without further purification. 1H NMR (250 MHz, CDCl3) δ8.70 (2H, br s), 7.92-7.91 (1H, d, J=2.2 Hz), 7.62-7.58 (1H, dd, J=8.5 Hz and 2.2 Hz), and 7.47-7.41 (3H, m), m/z (ES+) 318, 320 (M+1).

Workup

temperatureto cool to ambient temperature
additionpoured onto ice
extractionextracted with ethyl acetate (2×30 ml)
washthe combined organic layers were washed with water
dry with materialThe solution was dried over sodium sulphate
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-88309b8fa80c49a3a4d42da24057b53c
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06060469

Reaction notes

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