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

HRID 596136Notes

Reaction equation

HRID 596136 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

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%)

Workup

  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%)

Sources & evidence

ORD record
ord-1a409fc3acff45768e08846e6e7a21eb
Source dataset
uspto-grants-2016_01
Patent number
US09246103B2

Reaction notes

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