Dimethyl Ether → 2-(3-Bromophenyl)triphenylene

HRID 1499983Notes

Reaction equation

HRID 1499983 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:22][C:23]1[CH:24]=[C:25](I)[CH:26]=[CH:27][CH:28]=1.COC.C(=O)([O-])[O-].[Na+].[Na+]>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.C1(C)C=CC=CC=1>[Br:22][C:23]1[CH:24]=[C:25]([C:14]2[CH:15]=[CH:16][C:17]3[C:18]4[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=4)[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[C:12]=3[CH:13]=2)[CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 4

HCID 8254Dimethyl EtherHCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 59805119Triphenylen-2-ylboronic acid

Product 1

HCID 584720322-(3-Bromophenyl)triphenylene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, triphenylene-2-boronic acid (32.6 g), 3-bromoiodobenzene (28.1 g), tetrakistriphenylphosphinepalladium(0) (2.31 g), toluene (200 mL), DME (dimethylether) (200 mL) and an aqueous solution of 2M sodium carbonate (200 mL) were put in a flask and heated to reflux for 24 hours. After the reaction solution was cooled down to the room temperature, the reaction solution was extracted with toluene. After an aqueous phase was removed, an organic layer was washed with saturated saline. After the organic phase was drided with magnesium sulfate and concentrated, the obtained residue was refined by silica-gel column chromatography, so that 2-(3-bromophenyl)triphenylene (27.5 g) was obtained.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. extractionthe reaction solution was extracted with toluene
  4. customAfter an aqueous phase was removed
  5. washan organic layer was washed with saturated saline
  6. concentrationconcentrated
  7. customwas obtained

Sources & evidence

ORD record
ord-b0e502828558403f8aeba1e2076d8f5d
Source dataset
uspto-grants-2015_12
Patent number
US09203043B2

Reaction notes

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