N-bromobutanimide → 5-Bromo-2-methoxypyridine

HRID 1771939Notes

Reaction equation

HRID 1771939 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C1C(=O)N([Br:16])C(=O)C1>C(#N)C>[Br:16][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 742012-Methoxypyridine

Product 1

HCID 27348955-Bromo-2-methoxypyridineYield 84.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-methoxy-pyridine (100 g, 0.92 mole), NBS (180 g, 1.0 mole) in acetonitrile (1.0 L) was stirred at reflux for 21 h. TLC showed that the reaction was complete. The reaction mixture was cooled to room temperature and concentrated. ˜900 ml solvent was collected. The resulting suspension was filtered and washed with n-hexane (˜400 mL). The filtrate was concentrated again to afford crude product. The crude product was distilled at reduced pressure (30° C./˜0.3 mmHg) to afford the title compound as a clear oil (146 g, 84%). LCMS (m/z): 190.0 [M+1]+. 1H NMR (400 MHz, CDCl3): δ 3.90 (s, 3H), 6.65 (d, J=8.8 Hz, 1H), 7.62 (dd, J=8.8 Hz, 2.4 Hz, 1H), 8.19 (s, 1H).

Workup

  1. temperatureat reflux for 21 h
  2. concentrationconcentrated
  3. custom˜900 ml solvent was collected
  4. filtrationThe resulting suspension was filtered
  5. washwashed with n-hexane (˜400 mL)
  6. concentrationThe filtrate was concentrated again
  7. customto afford crude product
  8. distillationThe crude product was distilled at reduced pressure (30° C./˜0.3 mmHg)

Sources & evidence

ORD record
ord-929b3ebd1456414aa8f70252de0617fe
Source dataset
uspto-grants-2016_02
Patent number
US09249156B2

Reaction notes

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