m-Chloroperbenzoic acid → 3-Bromo-5-ethoxypyridine
Reaction equation
Cl[C:2]1C=C(C=CC=1)C(OO)=O.[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([O:19][CH2:20][CH3:2])[CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
As shown in step 2-iii of Scheme 2, 3-chloroperoxybenzoic acid (9.426 g, 42.06 mmol) was added to 3-bromo-5-methoxypyridine (4.25 g, 21 mmol) in 200 mL of DCM at RT. The reaction was stirred overnight and the mixture was washed with 200 mL of 2 N NaOH and 2×200 mL brine. The organic phase was dried over MgSO4, filtered and the volatiles removed under reduced pressure to provide 3-bromo-5-ethoxypyridine, 1-oxide (Compound 1002, 4.4 g): 1H NMR (CDCl3): δ 8.05 (s, 1H), 7.9 (s, 1H), 7.0 (s, 1H), 4.12 (q, 2H), 1.45 (t, 3H).
Workup
- washthe mixture was washed with 200 mL of 2 N NaOH and 2×200 mL brine
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered
- customthe volatiles removed under reduced pressure
Sources & evidence
- ORD record
- ord-bb33a77f3d104a1d9d4b28bfc16bc476
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524906B2
Reaction notes
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