Iodine → 5-Bromo-2-(7-bromo-9,9'-Dioctyl-9H-fluoren-2-yl)benzoic acid methyl ester

HRID 596136노트

반응식

HRID 596136 반응식
[CH3:1][O:2][C:3](=[O:40])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:13]=2[CH:12]=1.II.[Br:43]Br.[O-]S([O-])(=S)=O.[Na+].[Na+]>ClCCl>[CH3:1][O:2][C:3](=[O:40])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][C:17]([Br:43])=[CH:18][CH:19]=3)[C:14]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:13]=2[CH:12]=1

참가 물질

6

반응물 4

HCID 807IodineHCID 24408BromineHCID 24477Sodium ThiosulfateHCID 902507115-Bromo-2-(9,9'-Dioctyl-9H-fluoren-2-yl)benzoic acid methyl ester

생성물 1

HCID 867235505-Bromo-2-(7-bromo-9,9'-Dioctyl-9H-fluoren-2-yl)benzoic acid methyl ester수율 84%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

40 g (66 mmol) 15 is dissolved in 300 ml dichloromethane. The solution is cooled to 0° C., 1 g iodine is added and the mixture is stirred for 30 min. Then a solution of 11 g bromine in dichloromethane is slowly added by a dropping funnel. The solution is heated to reflux until the reaction is completed The reaction mixture is allowed to warm up to room temperature and of a 200 ml saturated Na2S2O3 solution is added. The organic layer is separated and the aqueous layer is extracted with dichloromethane. The unified organic layers are washed twice with 100 ml water dried over sodium sulfate, filtrated and the solvent is removed under vacuum. The residue is recystallisated from butanole to result white solid (38 g 55.6 mmol, yield: 84%)

후처리

  1. temperatureThe solution is heated
  2. temperatureto reflux until the reaction
  3. additionis added
  4. customThe organic layer is separated
  5. extractionthe aqueous layer is extracted with dichloromethane
  6. washThe unified organic layers are washed twice with 100 ml water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltrated
  9. customthe solvent is removed under vacuum
  10. customto result white solid (38 g 55.6 mmol, yield: 84%)

출처 및 근거

ORD 기록
ord-1a409fc3acff45768e08846e6e7a21eb
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09246103B2

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