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

HRID 1356532ノート

反応式

HRID 1356532 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

反応条件

温度
82.5 °C

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

出典と根拠

ORDレコード
ord-041cedc817c44ec4901ca20b22929206
出典データセット
uspto-grants-2003_07
特許番号
US06586594B1

反応ノート

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