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

HRID 2199262Notes

Reaction equation

HRID 2199262 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Br:9]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:9][CH2:8][C:5]1[CH:4]=[N:3][C:2]([Cl:1])=[N:7][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 5817192-Chloro-5-methylpyrimidine

Product 1

HCID 216979795-(Bromomethyl)-2-chloropyrimidineYield 38%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

In 30 ml of carbon tetrachloride, 1.04 g (8.13 mmol) of 2-chloro-5-methylpyrimidine was dissolved. To this solution, 1.73 g (9.75 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added, followed by heating under reflux for 6 hours. After completion of the reaction, the reaction liquid was returned to room temperature, and concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1). Thus, 641 mg of 5-bromomethyl-2-chloropyrimidine was obtained (Percentage Yield: 380).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. customAfter completion of the reaction
  4. customthe reaction liquid
  5. customwas returned to room temperature
  6. concentrationconcentrated under reduced pressure
  7. customThen, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-a3f0733e5cc94ae0be0a6fe3549b84e2
Source dataset
uspto-grants-2016_06
Patent number
US09357776B2

Reaction notes

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