1,2,4-Trimethylbenzene → 2-(Anthracen-9-yl)triphenylene

HRID 2179861Notes

Reaction equation

HRID 2179861 reaction equation
[CH:1]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][C:2]=1B(O)O.Br[C:23]1[C:24]2[C:29]([CH:30]=[C:31]3[C:36]=1[CH:35]=[CH:34][CH:33]=[CH:32]3)=[CH:28][CH:27]=[CH:26][CH:25]=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C(=CC(=CC=1)C)C)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)(C)(C)C>[CH:35]1[C:36]2[C:31](=[CH:30][C:29]3[C:24]([C:23]=2[C:14]2[CH:15]=[CH:16][C:17]4[C:18]5[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=5)[C:6]5[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=5)[C:12]=4[CH:13]=2)=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 4

HCID 72471,2,4-TrimethylbenzeneHCID 62657Potassium Phosphate, TribasicHCID 740629-BromoanthraceneHCID 59805119Triphenylen-2-ylboronic acid

Product 1

HCID 867013572-(Anthracen-9-yl)triphenyleneYield 59.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

Under the nitrogen atmosphere, triphenylen-2-ylboronic acid (5.6 g), 9-bromoanthracene (3.5 g), (Pd(PPh3)4) (0.5 g), potassium phosphate (5.8 g), and a mixture solvent of pseudo cumene, t-butyl alcohol, and water (48 ml) (pseudo cumene/t-butyl alcohol/water=10/1/1 (volume ratio)) were added to a flask and then refluxed for 8 hours. After adding water, the precipitates were collected by suction filtration. The obtained solid was washed with water followed by methanol and purified by silica gel column chromatography (solvent: toluene). After re-crystallization with a mixture solution of toluene/ethyl acetate, 2-(anthracen-9-yl)triphenylene (3.3 g) was obtained as an eleventh intermediate compound. The scheme is represented in the following “Reaction 21”.

Workup

  1. temperaturerefluxed for 8 hours
  2. filtrationthe precipitates were collected by suction filtration
  3. washThe obtained solid was washed with water
  4. custompurified by silica gel column chromatography (solvent: toluene)
  5. customAfter re-crystallization with a mixture solution of toluene/ethyl acetate

Sources & evidence

ORD record
ord-37c36c6b3dbf46e79cb0d4a12e44d24d
Source dataset
uspto-grants-2015_06
Patent number
US09070885B2

Reaction notes

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