Bromine → 6-(1-Bromoethyl)-2,4-dichloro-5-fluoropyrimidine

HRID 459416노트

반응식

HRID 459416 반응식
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([F:9])=[C:4]([CH2:10][CH3:11])[N:3]=1.[Br:12]N1C(=O)CCC1=O.BrBr>O>[Br:12][CH:10]([C:4]1[N:3]=[C:2]([Cl:1])[N:7]=[C:6]([Cl:8])[C:5]=1[F:9])[CH3:11]

참가 물질

5

반응물 3

HCID 24408BromineHCID 67184N-bromobutanimide2회HCID 223233532,4-Dichloro-6-ethyl-5-fluoropyrimidine

생성물 1

HCID 223233396-(1-Bromoethyl)-2,4-dichloro-5-fluoropyrimidine수율 95%

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

A mixture of the compound of part (i) (400 g), N-bromosuccinimide (730 g), azoisobutyronitrile (33.7 g), bromine (65.5 g) and water (6.4 L) was heated at 80–85° C. for 5 hours. Further N-bromosuccinimide (183 g) was added, heating continued for 2 hours then further azoisobutyronitrile (33.7 g) added. After heating for 2 hours at 85° C. further azoisobutyronitrile (33.7 g) was added and heating continued for 3 hours. The reaction was cooled, diluted with water (4 L) and extracted with dichloromethane (2×3 L). The combined organic extracts were washed with a solution of sodium metabisulphate (600 g) in water (2.5 L), followed by water (3 L). The solvent was removed by evaporation under reduced pressure, toluene (1.0 L) added and the solution concentrated under reduced pressure to give the product as an oil (534 g).

후처리

  1. temperaturewas heated at 80–85° C. for 5 hours
  2. temperatureheating
  3. additionwas added
  4. temperatureheating
  5. waitcontinued for 3 hours
  6. temperatureThe reaction was cooled
  7. extractionextracted with dichloromethane (2×3 L)
  8. washThe combined organic extracts were washed with a solution of sodium metabisulphate (600 g) in water (2.5 L)
  9. customThe solvent was removed by evaporation under reduced pressure, toluene (1.0 L)
  10. additionadded
  11. concentrationthe solution concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-fca3c9b202584e859da42c5504b3bb1d
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07193083B2

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