Water → Benzonitrile, 3-bromo-4-hydroxy-5-nitro-

HRID 921604

반응식

HRID 921604 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8](Br)[C:9]=1[OH:10])[C:5]#[N:6].[N:12]([O-:14])=[O:13].[Na+].BrBr.O>C(O)(=O)C.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:12]([O-:14])=[O:13])[C:9]=1[OH:10])[C:5]#[N:6]

참가 물질

7

반응물 4

HCID 962WaterHCID 15531BromoxynilHCID 24408BromineHCID 23668193Sodium Nitrite

생성물 1

HCID 3014048Benzonitrile, 3-bromo-4-hydroxy-5-nitro-수율 84.2%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

반응 조건

온도
50 °C

실험 절차

(I1B): To a suspension of 3,5-dibromo-4-hydroxybenzonitrile (2.11 g, 7.62 mmol) in acetic acid (70 mL) was added sodium nitrite (2.63 g, 38.1 mmol) in small portion, evolving bubbles and bromine were observed. After addition, the mixture was stirred at 50° C. overnight. Reaction was cooled to room temperature; water (250 ml) was added and extracted with EtOAc for two times. The combined extracts were washed with water and brine, dried over MgSO4 filtered and the filtrate was concentrated to give yellow orange solid. The solid was treated with small amount of MeOH, collected by filtration, rinsed with MeOH, dried to afford 1.56 g of 3-bromo-4-hydroxy-5-nitrobenzonitrile as yellow solid.

후처리

  1. additionAfter addition
  2. customReaction
  3. temperaturewas cooled to room temperature
  4. extractionextracted with EtOAc for two times
  5. washThe combined extracts were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customto give yellow orange solid
  10. filtrationcollected by filtration
  11. washrinsed with MeOH
  12. customdried

출처 및 근거

ORD 기록
ord-5e4a41f8365944babdc5abdc1a0e4049
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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