Hydrogen Bromide → 4-Bromo-1-ethyl-2-nitrobenzene

HRID 43325노트

반응식

HRID 43325 반응식
[CH2:1]([C:3]1[CH:9]=[CH:8][C:6](N)=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11])[CH3:2].N([O-])=O.[Na+].[BrH:17]>O>[Br:17][C:6]1[CH:8]=[CH:9][C:3]([CH2:1][CH3:2])=[C:4]([N+:10]([O-:12])=[O:11])[CH:5]=1

참가 물질

5

반응물 3

HCID 260Hydrogen Bromide2회HCID 227086804-Ethyl-3-nitroanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 75669964-Bromo-1-ethyl-2-nitrobenzene

시약·촉매·용매 1

HCID 962Water용매2회

반응 조건

온도
-5 °C

실험 절차

Hydrobromic acid (48% wt. in water, 240 ml) is added dropwise to a suspension of 4-ethyl-3-nitroaniline (20 g, 0.12 mol) in water (80 ml), and the mixture stirred until the solid is dissolved. The mixture is cooled to −5° C. and a solution of sodium nitrite (19.8 g, 0.28 mol) in water (100 ml) is added dropwise, maintaining the temperature at 0-5° C. Once the addition is complete, the cooling bath is removed and the reaction mixture is stirred for one hour at room temperature. The mixture is added dropwise to a pre-cooled solution of cuprous bromide (22.4 g, 0.16 mol) in hydrobromic acid (48% wt. in water) at 0° C. The reaction mixture is stirred and allowed to warm to room temperature over three hours. The mixture is extracted with diethyl ether, and the organic extracts are combined, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo. The residue is further purified by column chromatography on silica gel, eluting with hexane to give 4-bromo-1-ethyl-2-nitrobenzene (18 g).

후처리

  1. dissolutionis dissolved
  2. temperaturemaintaining the temperature at 0-5° C
  3. additionOnce the addition
  4. customthe cooling bath is removed
  5. stirringthe reaction mixture is stirred for one hour at room temperature
  6. stirringThe reaction mixture is stirred
  7. temperatureto warm to room temperature over three hours
  8. extractionThe mixture is extracted with diethyl ether
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationthe filtrate concentrated in vacuo
  12. customThe residue is further purified by column chromatography on silica gel
  13. washeluting with hexane

출처 및 근거

ORD 기록
ord-ccf2738d93d64552b45d91a18f557485
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536351B2

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