Potassium Carbonate → 4'-Bromo-2-nitrobiphenyl

HRID 1022356Notes

Reaction equation

HRID 1022356 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Br:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>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.COCCOC.O>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69115o-IodonitrobenzeneHCID 79599(4-Bromophenyl)boronic acid

Product 1

HCID 218576474'-Bromo-2-nitrobiphenyl

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

o-iodonitrobenzene (9.42 g, 37.84 mmol), 4-bromobenzeneboronic acid (7.6 g, 37.84 mmol), potassium carbonate (21 g, 151.36 mmol) was added to 190 mL DME/water (3:2) solution and degassed for 30 minutes. Pd(PPh3)4 (437 mg, 0.38 mmol) was added to the slurry under nitrogen and the slurry was degassed for another 5 minutes. The reaction was refluxed under nitrogen for 6 h. Content of the flask was filtered through a pad of celite and partitioned in ethyl acetate and brine. Organic phase was dried over anhydrous Na2SO4 and evaporated under vacuum. Crude yellow oil was flashed over silica gel using 5% ethylacetate/hexane. Final compound was isolated as colorless oil (9.8 g, 35.4 mmol).

Workup

  1. customdegassed for 30 minutes
  2. customthe slurry was degassed for another 5 minutes
  3. temperatureThe reaction was refluxed under nitrogen for 6 h
  4. filtrationContent of the flask was filtered through a pad of celite
  5. custompartitioned in ethyl acetate
  6. dry with materialOrganic phase was dried over anhydrous Na2SO4
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-d8d50ae060164355b1650d98696e8934
Source dataset
uspto-grants-2014_05
Patent number
US08722205B2

Reaction notes

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