Sodium Thiosulfate → 2-(10-Bromoanthracen-9-yl)triphenylene

HRID 2179862Notes

Reaction equation

HRID 2179862 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]2[CH:32]=[CH:31][C:30]4[C:29]5[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=5)[C:23]5[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=5)[C:17]=4[CH:16]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[Br:33]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>II.C1COCC1>[Br:33][C:6]1[C:5]2[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=2)[C:13]([C:15]2[CH:32]=[CH:31][C:30]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]=3[CH:16]=2)=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[CH:11]2

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 867013572-(Anthracen-9-yl)triphenylene

Product 1

HCID 867013582-(10-Bromoanthracen-9-yl)triphenyleneYield 88.8%

Reagents, catalysts & solvents 2

HCID 807IodineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under the nitrogen atmosphere, 2-(anthracen-9-yl)triphenylene (3.3 g) as the eleventh intermediate compound, N-bromosuccinimide (NBS) (1.7 g), iodine (0.1 g) and THF (25 ml) were added to a flask, and stirred at room temperature for 5 hours. An aqueous solution of sodium thiosulfate was added and the reaction was terminated. The precipitates were collected by suction filtration. The obtained solid was washed with methanol and subsequently with heptane and purified by silica gel column chromatography (solvent: toluene) to give 2-(10-bromoanthracen-9-yl)triphenylene (3.5 g) as a twelfth intermediate compound. The scheme is shown in the following “Reaction 22”.

Workup

  1. customthe reaction was terminated
  2. filtrationThe precipitates were collected by suction filtration
  3. washThe obtained solid was washed with methanol and subsequently with heptane
  4. custompurified by silica gel column chromatography (solvent: toluene)

Sources & evidence

ORD record
ord-be85ceab0e8c4df4bde8abdf2f5fa34d
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

Loading…