Methyl Ethyl Ketone → 4-(Benzyloxy)-4'-bromo-1,1'-biphenyl

HRID 1936336노트

반응식

HRID 1936336 반응식
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].C(C(C)=O)C>O1CCCC1>[CH2:1]([O:22][C:19]1[CH:18]=[CH:17][C:16]([C:13]2[CH:14]=[CH:15][C:10]([Br:9])=[CH:11][CH:12]=2)=[CH:21][CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 6569Methyl Ethyl KetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 950934-Bromo-4'-hydroxybiphenyl

생성물 1

HCID 224657734-(Benzyloxy)-4'-bromo-1,1'-biphenyl수율 85.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

First, 25.0 g of benzyl bromide, 36.42 g of 4′-bromo-4-hydroxybiphenyl, 36.4 g of potassium carbonate, and 300 ml of methyl ethyl ketone were put in a1 flask, and stirred under reflux for six hours. After the reaction, 300 ml of tetrahydrofuran was added to the reaction solution, and a mixture was cooled to ambient temperature. Insoluble material was filtered off, and toluene was added to the filtrate to separate an organic layer. The organic layer was washed with a saturated brine and dried with sodium sulfate. The solvent was then distilled off. The residue was recrystallized from acetone, to obtain 42.56 g (Y: 85.8%) of 4-benzyloxy-4′-bromobiphenyl. The purity of the resultant compound was 99.0% as measured by GC.

후처리

  1. temperatureunder reflux for six hours
  2. additionwas added to the reaction solution
  3. filtrationInsoluble material was filtered off
  4. additiontoluene was added to the filtrate
  5. customto separate an organic layer
  6. washThe organic layer was washed with a saturated brine
  7. dry with materialdried with sodium sulfate
  8. distillationThe solvent was then distilled off
  9. customThe residue was recrystallized from acetone

출처 및 근거

ORD 기록
ord-ca6103f2dd4f45f2894ab0de8930d9e6
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06388146B1

반응 노트

불러오는 중…