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

HRID 459416ノート

反応式

HRID 459416 の反応式
[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]

参加物

5

反応物 3

HCID 24408BromineHCID 67184N-bromobutanimide2 回HCID 223233532,4-Dichloro-6-ethyl-5-fluoropyrimidine

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fca3c9b202584e859da42c5504b3bb1d
出典データセット
uspto-grants-2007_03
特許番号
US07193083B2

反応ノート

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