Acetic Acid → 2-Bromo-4-(bromomethyl)pyridine

HRID 899988Notes

Reaction equation

HRID 899988 reaction equation
C(O)(=O)C.[Br: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>[Br: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 27340872-Bromo-4-methylpyridine

Product 1

HCID 129548062-Bromo-4-(bromomethyl)pyridineYield 28.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
50 °C

Procedure

0.073 ml of acetic acid is added to a solution of 0.172 g of 2-bromo-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 brought, with stirring, to a temperature of 50° C. 0.356 g of N-bromosuccinimide and 0.048 g of benzoyl peroxide are added successively at this temperature. The mixture is maintained at 80° C. for about 18 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 30 and 40 ml are concentrated to dryness under reduced pressure. 0.071 g of 2-bromo-4-(bromomethyl)pyridine is thus obtained.

Workup

  1. temperatureThe mixture is maintained at 80° C. for about 18 hours
  2. temperatureAfter cooling
  3. washeluted with dichloromethane at a flow rate of 5 ml/minute
  4. concentrationThe fractions between 30 and 40 ml are concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-228773cad6b54e8986dea8ee8544a588
Source dataset
uspto-grants-2008_04
Patent number
US07354933B2

Reaction notes

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