Triphenylene → 2-Bromotriphenylene

HRID 2281110Notes

Reaction equation

HRID 2281110 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][CH:2]=1.[Br:19]Br>P(OC)(OC)(OC)=O>[Br:19][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[CH:1]=1

Participants

4

Reactant 2

HCID 9170TriphenyleneHCID 24408Bromine

Product 1

HCID 183811742-BromotriphenyleneYield 69.8%

Reagents, catalysts & solvents 1

HCID 10541Trimethyl PhosphateSolvent2×

Conditions

Temperature
80 °C

Procedure

3.2 g (14 mmol) of triphenylene was dissolved in 60 mL of trimethyl phosphate. To the suspension was added 2.23 g (14 mmol) of bromine in 10 mL of trimethyl phosphate at room temperature under N2. The mixture was then heated up to 80° C. The reaction was monitored by HPLC. The reaction was quenched by pouring into ice water, then extracted with dichloromethane and washed with saturated sodium bisulfite solution. After drying with magnesium sulfate, the solvent was evaporated. The crude product was run through a short silica gel plug using dichloromethane. 3.0 g of product was obtained after drying under vacuum. The product contains triphenylene, 1-bromotriphenylene, 2-bromotriphenylene, and a mixture of dibromotriphenylene isomers.

Workup

  1. customThe reaction was quenched
  2. additionby pouring into ice water
  3. extractionextracted with dichloromethane
  4. washwashed with saturated sodium bisulfite solution
  5. dry with materialAfter drying with magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-05230fbb9cf746e5884e472c3e17b3ec
Source dataset
uspto-grants-2015_09
Patent number
US09139494B2

Reaction notes

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