N-bromobutanimide → 5-(Bromomethyl)-2-fluoropyridine

HRID 1621393Notes

Reaction equation

HRID 1621393 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[F:9][C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=1>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:8][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([F:9])=[N:11][CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 27746352-Fluoro-5-methylpyridine

Product 1

HCID 220506385-(Bromomethyl)-2-fluoropyridineYield 61.5%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

Benzoyl peroxide (1.570 g, 6.48 mmol) and NBS (23.19 g, 130 mmol) was added to a stirred solution of 2-fluoro-5-methylpyridine (SynQuest Labs, Inc., Alachua, Fla., 14.4045 g, 130 mmol) in CCl4 (125 mL) and the suspension was heated at reflux for 2 h. After cooling, the solution was filtered to remove solid and concentrated, and the residue was purified by flash column chromatography (ISCO Combiflash system, Teledyne ISCO, Lincoln, Nebr., hexanes to 10% ethyl acetate in hexanes) to give 5-(bromomethyl)-2-fluoropyridine (15.11 g, 80 mmol, 61.3% yield) as a yellow solid. LCMS (API-ES) m/z 191 (M+H)+.

Workup

  1. temperaturethe suspension was heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. filtrationthe solution was filtered
  5. customto remove solid
  6. concentrationconcentrated
  7. customthe residue was purified by flash column chromatography (ISCO Combiflash system, Teledyne ISCO, Lincoln, Nebr., hexanes to 10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-705d9930a894435788bbed6876a81dee
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

Loading…