Bromine → Andecaliximab

HRID 1057003노트

반응식

HRID 1057003 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 56776542Andecaliximab수율 99.3%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 516892Sodium Bicarbonate용매

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온도
55 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4236b756814f442285e1fcaec61f1c8a
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399640B2

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