Benzyl Bromide → 1-(Benzyloxy)-3-bromo-5-nitrobenzene

HRID 712146노트

반응식

HRID 712146 반응식
[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CC(C)=O>[CH2:18]([O:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([Br:1])[CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 104889843-Bromo-5-nitrophenol

생성물 1

HCID 147841491-(Benzyloxy)-3-bromo-5-nitrobenzene수율 51%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 3-bromo-5-nitro-phenol (770 g, 3.53 mol) in acetone (10 L) was added pulverized K2CO3 (2.45 kg, 17.75 mol) in one portion at rt followed by addition of benzyl bromide (632 mL, 5.32 mol) over a period of 30 min. The resulting reaction mixture was stirred for 15 min then heated at reflux for 3 h. After reaction completion (by TLC), the reaction mixture was filtered through celite and the acetone distilled off. The crude residue thus obtained was purified over silica gel (60-120 M) using EtOAc:hexane (5:95) to obtain the desired product (551 g, 51%).

후처리

  1. customat rt
  2. customThe resulting reaction mixture
  3. temperaturethen heated
  4. temperatureat reflux for 3 h
  5. customAfter reaction completion (by TLC)
  6. filtrationthe reaction mixture was filtered through celite
  7. distillationthe acetone distilled off
  8. customThe crude residue thus obtained
  9. customwas purified over silica gel (60-120 M)

출처 및 근거

ORD 기록
ord-c3c5112d04e34992a02df5f456b13ae7
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181234B2

반응 노트

불러오는 중…