N-bromobutanimide → 5-Bromo-2-methoxypyridine

HRID 1399947Notes

Reaction equation

HRID 1399947 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 reaction 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 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. customreaction complete
  3. concentrationconcentrated
  4. custom˜900 ml solvent was collected
  5. filtrationThe resulting suspension was filtered
  6. washwashed with n-hexane (˜400 mL)
  7. concentrationThe filtrate was concentrated again
  8. customto afford crude product
  9. distillationThe crude product was distilled at reduced pressure (30° C./˜0.3 mmHg)

Sources & evidence

ORD record
ord-f7af0fd1bad34e6ebc4f61456091128d
Source dataset
uspto-grants-2014_12
Patent number
US08906909B2

Reaction notes

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