Bromine → Andecaliximab

HRID 1057003ノート

反応式

HRID 1057003 の反応式
[Br:1]Br.[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:5]=1[N+:12]([O-:14])=[O:13]>C(O)(=O)C.C(=O)(O)[O-].[Na+]>[Br:1][C:9]1[CH:8]=[CH:7][C:6]([O:10][CH3:11])=[C:5]([N+:12]([O-:14])=[O:13])[C:4]=1[F:3]

参加物

5

反応物 2

HCID 24408BromineHCID 27827761-Fluoro-3-methoxy-2-nitrobenzene

生成物 1

HCID 56776542Andecaliximab収率 99.3%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
55 °C

実験手順

Bromine (1.55 mL, 30.1 mmol) was added dropwise to a solution of 1-fluoro-3-methoxy-2-nitrobenzene (1.29 g, 7.53 mmol) in acetic acid (15.1 mL). The reaction mixture was warmed to 55° C. and stirred at 55° C. for 17 h, after which time the reaction mixture was concentrated in vacuo to give a crude solid. The crude solid was diluted with saturated sodium bicarbonate solution and extracted with ethyl acetate. Layers were separated and the organic layer was washed with saturated sodium bicarbonate solution, dried with sodium sulfate, filtered, and concentrated in vacuo to give the desired product (1.87 g, 99%) as a yellow solid that was used in further step without purification.

後処理

  1. concentrationafter which time the reaction mixture was concentrated in vacuo
  2. customto give a crude solid
  3. extractionextracted with ethyl acetate
  4. customLayers were separated
  5. washthe organic layer was washed with saturated sodium bicarbonate solution
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4236b756814f442285e1fcaec61f1c8a
出典データセット
uspto-grants-2016_07
特許番号
US09399640B2

反応ノート

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