Sodium Thiosulfate → 9-([2,2'-Binaphthalen]-7-yl)-10-bromoanthracene

HRID 2179855Notes

Reaction equation

HRID 2179855 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:12]4[C:17]([CH:18]=[C:19]5[C:24]=3[CH:23]=[CH:22][CH:21]=[CH:20]5)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1.[Br:35]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>II.C1COCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[C:12]4[C:17]([C:18]([Br:35])=[C:19]5[C:24]=3[CH:23]=[CH:22][CH:21]=[CH:20]5)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 867013539-([2,2'-Binaphthalen]-7-yl)anthracene

Product 1

HCID 867013529-([2,2'-Binaphthalen]-7-yl)-10-bromoanthraceneYield 93%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under the nitrogen atmosphere, 9-([2,2′-binaphthalen]-7-yl) anthracene (10.0 g) as the ninth intermediate compound, N-bromosuccinimide (NBS) (4.6 g), iodine (0.1 g), and THF (60 ml) were added to a flask and stirred overnight at room temperature. By adding an aqueous solution of sodium thiosulfate, the reaction was terminated. Liquid separation was performed by adding water and toluene. Subsequently, the solid obtained by distillation of the organic layer under reduced pressure was purified by silica gel column chromatography (solvent: toluene). The solid obtained by distillation of the solvent under reduced pressure was washed with heptane to give 9-([2,2′-binaphthalen]-7-yl)-10-bromoanthracene (11.0 g) as a tenth intermediate compound. The scheme is shown in the following “Reaction 15”.

Workup

  1. customthe reaction was terminated
  2. customLiquid separation
  3. additionby adding water and toluene
  4. customSubsequently, the solid obtained by distillation of the organic layer under reduced pressure
  5. customwas purified by silica gel column chromatography (solvent: toluene)
  6. customThe solid obtained by distillation of the solvent under reduced pressure
  7. washwas washed with heptane

Sources & evidence

ORD record
ord-3ff47926326d4d8491c893f22d65442e
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

Loading…