Potassium Carbonate → 1-([1,1'-Biphenyl]-3-yl)-6-bromopyrene

HRID 929283Notes

Reaction equation

HRID 929283 reaction equation
[Br:1][C:2]1[C:15]2[C:16]3=[C:17]4[C:12](=[CH:13][CH:14]=2)[CH:11]=[CH:10][C:9](Br)=[C:8]4[CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=1.[C:19]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:24]=[CH:23][CH:22]=[C:21](B(O)O)[CH:20]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.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:19]1([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:24]=[CH:23][CH:22]=[C:21]([C:9]2[C:8]3[C:17]4=[C:16]5[C:5](=[CH:6][CH:7]=3)[CH:4]=[CH:3][C:2]([Br:1])=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)[CH:20]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 176470Pyrene, 1,6-Dibromo-HCID 2734315(3-Phenylphenyl)boronic acid

Product 1

HCID 1180062971-([1,1'-Biphenyl]-3-yl)-6-bromopyreneYield 70%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1,6-dibromopyrene (5.4 g, 15.0 mmol), [1,1′-biphenyl]-3-ylboronic acid (3.3 g, 16.5 mmol), and K2CO3 (10.4 g, 75.0 mmol) in 1,4-dioxane (320 mL) and water (50 mL) was bubbled with nitrogen for 15 min. Pd(PPh3)4 (0.87 g, 0.75 mmol) was then added to the mixture. The mixture was bubbled with nitrogen for 15 min. The resultant mixture was refluxed for 19 h. The reaction mixture was then extracted by DCM. The extracts were dried over MgSO4 and the solvent was removed in vacuo. The residue was purified by flash chromatography using 15% DCM/hexane (containing 0.25% triethylamine) to yield 1-([1,1′-biphenyl]-3-yl)-6-bromopyrene (4.5 g, 70% yield) as a white solid.

Workup

  1. customThe mixture was bubbled with nitrogen for 15 min
  2. temperatureThe resultant mixture was refluxed for 19 h
  3. extractionThe reaction mixture was then extracted by DCM
  4. dry with materialThe extracts were dried over MgSO4
  5. customthe solvent was removed in vacuo
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-eb5deb5b01914b1790d7d3f2d3ecb936
Source dataset
uspto-grants-2016_03
Patent number
US09293712B2

Reaction notes

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