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

HRID 496817ノート

反応式

HRID 496817 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b666533fb9c34ffb927a4fbf9ee4e6de
出典データセット
uspto-grants-2005_09
特許番号
US06946555B2

反応ノート

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