Toluene → HCID 86761805, compound

HRID 1968386Notes

Reaction equation

HRID 1968386 reaction equation
[C:1]1(B(O)O)[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[C:26]1([CH3:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>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>[C:26]1([CH:32]2[CH:5]([C:4]3[CH:15]=[CH:14][CH:1]=[CH:2][CH:3]=3)[C:6]3[CH:7]=[CH:8][C:9]([C:15]4[C:8]5[C:7]6=[C:16]7[C:11](=[CH:10][CH:9]=5)[CH:12]=[CH:13][CH:14]=[C:1]7[CH:2]=[CH:3][C:6]6=[CH:5][CH:4]=4)=[CH:10][C:32]=3[C:26]3[C:31]2=[CH:30][CH:29]=[C:28]([C:14]2[C:1]4[C:16]5=[C:7]6[C:6](=[CH:3][CH:2]=4)[CH:5]=[CH:4][CH:15]=[C:8]6[CH:9]=[CH:10][C:11]5=[CH:12][CH:13]=2)[CH:27]=3)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 5084102Pyren-1-ylboronic acid

Product 1

HCID 86761805HCID 86761805, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
60 °C

Procedure

As illustrated in Formula 7, the product 4a in Formula 6 (1.0 g, 2.05 mmol), 1-pyreneboronic acid (1.53 g, 6.2 mmol), potassium carbonate solution (2.0 M, 10 mL), and dried toluene (30 mL) were charged in a two-necked bottle. The bottle was deoxygenated and purged with nitrogen, and the mixture in the bottle was stirred at 60° C. until it was totally dissolved. The nitrogen pressure of the bottle was increased, and Pd(PPh3)4 (243 mg, 0.21 mmol) was rapidly added into the bottle. The reaction was heated to 110° C., and stirred for 48 hours. The resulting mixture was cooled to room temperature to precipitate a solid, and the solid was collected by filtering. The solid was sublimated at a temperature of 330° C. to obtain a white solid of 1.03 g (yield=69%).

Workup

  1. customThe bottle was deoxygenated
  2. custompurged with nitrogen
  3. dissolutionwas totally dissolved
  4. temperatureThe nitrogen pressure of the bottle was increased
  5. temperatureThe reaction was heated to 110° C.
  6. stirringstirred for 48 hours
  7. temperatureThe resulting mixture was cooled to room temperature
  8. customto precipitate a solid
  9. customthe solid was collected
  10. filtrationby filtering
  11. customwas sublimated at a temperature of 330° C.
  12. customto obtain a white solid of 1.03 g (yield=69%)

Sources & evidence

ORD record
ord-b501fc1958074ad083e26767f54bf3dd
Source dataset
uspto-grants-2013_04
Patent number
US08426039B2

Reaction notes

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