Dichloromethane → 4-(1-Bromoethyl)-6-chloro-5-fluoropyrimidine

HRID 1356531Notes

Reaction equation

HRID 1356531 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1.[Br:11]N1C(=O)CCC1=O.ClCCl>O>[Br:11][CH:9]([C:6]1[N:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=1[F:8])[CH3:10]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 167434454-Chloro-6-ethyl-5-fluoropyrimidine

Product 1

HCID 109116334-(1-Bromoethyl)-6-chloro-5-fluoropyrimidineYield 107.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A stirred mixture of the compound of part (v) (38.5 kg), azoisobutyronitrile (AIBN) (1.92 kg), N-bromosuccinimide (49 kg) and dichloromethane (198 L) was heated under reflux under nitrogen for 12 hours. The mixture was cooled to 25° C. and water (239 L) added. The layers were separated and the aqueous layer extracted with dichloromethane (120 L). The combined organic layers were washed with a solution of sodium metabisulphite (22.8 kg) in water (239 L), followed by water (239 L). The organic layer was concentrated under reduced pressure, toluene (240 L) was added and the resulting solution concentrated under reduced pressure to give the product as an oil (61.7 kg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for 12 hours
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with dichloromethane (120 L)
  5. washThe combined organic layers were washed with a solution of sodium metabisulphite (22.8 kg) in water (239 L)
  6. concentrationThe organic layer was concentrated under reduced pressure, toluene (240 L)
  7. additionwas added
  8. concentrationthe resulting solution concentrated under reduced pressure

Sources & evidence

ORD record
ord-b55df029b2934a22a639d15b41dc0a09
Source dataset
uspto-grants-2003_07
Patent number
US06586594B1

Reaction notes

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