Dichloromethane → 5-Bromo-2-(bromomethyl)pyrimidine

HRID 712231Notes

Reaction equation

HRID 712231 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH3:8])=[N:6][CH:7]=1.CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:28])C(=O)C1.C(Cl)Cl>C(Cl)(Cl)(Cl)Cl.CCCCCC>[Br:1][C:2]1[CH:3]=[N:4][C:5]([CH2:8][Br:28])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 143877445-Bromo-2-methylpyrimidine

Product 1

HCID 205577975-Bromo-2-(bromomethyl)pyrimidineYield 25.5%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

To an ice-cold solution of 5-bromo-2-methylpyrimidine (3.5 g, 20.23 mmol) in CCl4 (20 mL) was added AIBN (0.14 g, 2.02 mmol) followed by portion wise addition of NBS (3.6 g, 20.23 mmol) and the mixture stirred at 70° C. for 30 h. After completion of reaction (by TLC), DCM (150 mL) was added and washed with water and brine. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified over 100-200 M silica-gel using 2% EtOAc:hexane to obtain the desired product (1.30 g, 25% yield). 1H NMR (CDCl3): δ 4.68 (s, 2H) and 9.03 (s, 2H).

Workup

  1. additionwas added
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified over 100-200 M silica-gel

Sources & evidence

ORD record
ord-06da0a75b61d4a688cbd2e19bc5f5d7f
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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