m-Chloroperbenzoic acid → 3-Bromo-5-ethoxypyridine

HRID 39350

Reaction equation

HRID 39350 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]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 8171633-Bromo-5-methoxypyridine

Product 1

HCID 122934803-Bromo-5-ethoxypyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. washthe mixture was washed with 200 mL of 2 N NaOH and 2×200 mL brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customthe volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-bb33a77f3d104a1d9d4b28bfc16bc476
Source dataset
uspto-grants-2013_09
Patent number
US08524906B2

Linked notes

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