Tetrahydrofuran → 1-Phenylpyrene

HRID 1429310Notes

Reaction equation

HRID 1429310 reaction equation
Br[C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][CH:9]=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[C:18]1([C:9]2[C:8]3[C:17]4=[C:16]5[C:5](=[CH:6][CH:7]=3)[CH:4]=[CH:3][CH:2]=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 1596271-Bromopyrene

Product 1

HCID 6242141-Phenylpyrene

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

1-bromopyrene (2 g, 7.11 mmol) and phenylboronic acid (1.40 g, 14.30 mmol) were put into a 2-neck round bottom flask filled with 80 ml of anhydrous tetrahydrofuran and stirred. Tetrakis(triphenylphosphine) palladium (0.41 g, 5 mol %), 20 g of potassium carbonate and 80 ml of distilled water were added into the same flask, which was then subjected to reflux at a temperature of 100° C. for 24 hours. After completion of the reaction, the tetrahydrofuran was removed and thusly generated solid was filtered. The filtered solid was recrystallized by dichloromethane and ethanol, thereby synthesizing 1-phenylpyrene (1.84 g, 93%).

Workup

  1. customAfter completion of the reaction
  2. customthe tetrahydrofuran was removed
  3. filtrationthusly generated solid was filtered
  4. customThe filtered solid was recrystallized by dichloromethane and ethanol
  5. customsynthesizing 1-phenylpyrene (1.84 g, 93%)

Sources & evidence

ORD record
ord-45ed20ab42fd4cf4b35729f710b3ae00
Source dataset
uspto-grants-2015_01
Patent number
US08940409B2

Reaction notes

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