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

HRID 496817노트

반응식

HRID 496817 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
25 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b666533fb9c34ffb927a4fbf9ee4e6de
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06946555B2

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