N-bromobutanimide → 2-Bromoacetyl-5-fluoro-6-methyl-pyridine

HRID 406273Notes

Reaction equation

HRID 406273 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([CH3:13])[N:7]=1)=[CH2:5])C.[Br:14]N1C(=O)CCC1=O>C1COCC1.O>[Br:14][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]([CH3:13])[N:7]=1)=[O:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 673246662-(1-Ethoxy-ethenyl)-5-fluoro-6-methyl-pyridine

Product 1

HCID 866725022-Bromoacetyl-5-fluoro-6-methyl-pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(1-ethoxy-ethenyl)-5-fluoro-6-methyl-pyridine obtained from Step A (15.3 g) in THF (200 mL) and water (8 mL) was treated with N-bromosuccinimide (12.02 g) at room temperature. After stirring for 10 min, the reaction was concentrated in vacuo. The resulting residue was purified by silica gel chromatography (eluted with a gradient of ethyl acetate in hexanes) to give 2-bromoacetyl-5-fluoro-6-methyl-pyridine, together with an unidentified impurity. This product was used in the next step. 1H NMR (500 MHz, CDCl3): δ 7.98 (dd, 1H), 7.44 (t, 1H), 4.83 (s, 2H), 2.57 (d, 3H).

Workup

  1. concentrationthe reaction was concentrated in vacuo
  2. customThe resulting residue was purified by silica gel chromatography (
  3. washeluted with a gradient of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2016664b5d8646b49c5838d8adeef732
Source dataset
uspto-grants-2014_06
Patent number
US08754099B2

Reaction notes

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