Sodium Hydroxide → HCID 18787029, compound

HRID 1107300Notes

Reaction equation

HRID 1107300 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:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=1.[Br:18]([O-])(=O)=O.[K+].[OH-].[Na+]>>[Br:18][C:9]1[CH:8]=[C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:6]=[CH:5][C:4]=1[O:3][C:2]([F:1])([F:16])[F:17]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 18787048HCID 18787048, compoundHCID 23673461Potassium Bromate

Product 1

HCID 18787029HCID 18787029, compoundYield 74%

Conditions

Temperature
0 °C

Procedure

3-(4-Trifluoromethoxyphenyl)pyridine (Description 61) (1.26 g, 5.27 mmol) was suspended in aqueous sulfic acid (50%, 16 ml) and cooled to 0° C. Potassium bromate (0.88 g, 5.27 mmol) was added in portions over 2 hours and the mixture was stirred at room temperature for 40 min. The mixture was poured into ice/water and basified with aqueous sodium hydroxide (4M). The mixture was extracted with ethyl acetate (3×100 ml) and the combined organic fractions were washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/ether (60:40) to give the title compound as an oil (1.2 g, 74%). 1H NMR (360 MHz, CDCl3) δ 8.82 (1H, s), 8.62 (1H, d), 7.84 (2H, m), 7.54 (1H, dd, J=8.5, 2.2 Hz), 7.41 (2H, m). m/z (ES+) 318, 320 (M+1).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (3×100 ml)
  2. washthe combined organic fractions were washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with hexane/ether (60:40)

Sources & evidence

ORD record
ord-803cefd401df4da3b33ca11ce30559f1
Source dataset
uspto-grants-2000_05
Patent number
US06060469

Reaction notes

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