Acetic Acid → 4-Bromomethyl-2-fluoropyridine

HRID 899989Notes

Reaction equation

HRID 899989 reaction equation
C(O)(=O)C.[F:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][N:7]=1.[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[F:5][C:6]1[CH:11]=[C:10]([CH2:12][Br:13])[CH:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 27374032-Fluoro-4-methylpyridine

Product 1

HCID 139851684-Bromomethyl-2-fluoropyridineYield 33.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
50 °C

Procedure

0.073 ml of acetic acid is added to a solution of 0.111 g of 2-fluoro-4-methylpyridine in 2.5 ml of carbon tetrachloride, under an inert atmosphere of argon at a temperature in the region of 20° C. The mixture is brought, with stirring, to a temperature of 50° C. 0.356 g of N-bromosuccinimide and 0.048 g of benzoyl peroxide are successively added at this temperature. The mixture is brought to 80° C. over about 16 hours. After cooling, the reaction medium is placed on a cartridge 20 mm in diameter packed with 10 g of 20-40 μm silica not conditioned beforehand, and then eluted with dichloromethane at a flow rate of 5 ml/minute. The fractions between 28 and 38 ml are concentrated to dryness under reduced pressure. 0.063 g of 2-fluoro-4-(bromomethyl)pyridine is thus obtained.

Workup

  1. temperatureAfter cooling
  2. washeluted with dichloromethane at a flow rate of 5 ml/minute
  3. concentrationThe fractions between 28 and 38 ml are concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-c5c8fc2367a04c2c9436170a6fd48184
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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