Sodium Carbonate → 2-Bromo-4'-chloro-1,1'-biphenyl

HRID 1476263Notes

Reaction equation

HRID 1476263 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[Br:14].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1.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>[Br:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:19]1[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 114141,2-DibromobenzeneHCID 742994-Chlorophenylboronic acid

Product 1

HCID 129394052-Bromo-4'-chloro-1,1'-biphenylYield 71%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Sodium carbonate (19.8 g, 186.81 mmol) and tetrakis(triphenylphosphine)palladium(0) (1.05 g, 0.90 mmol) were added to a solution of 1,2-dibromobenzene (12.8 ml, 105.98 mmol) and 4-chlorophenylboronic acid (14.1 g, 90.08 mmol) in toluene (170 ml) and water (80 ml). The mixture was purged with nitrogen and heated at reflux overnight. The reaction mixture was allowed to cool to room temperature, and partitioned between saturated aq. NH4Cl and ethyl acetate (500 ml). The organic layer was dried over MgSO4, filtered and the volatiles were evaporated under reduced pressure to give a residue. The residue was purified by column chromatography (ISCO, 330 g silica gel column, eluting with 100% hexanes) to give the title product (17.0 g, yield: 71%).

Workup

  1. customThe mixture was purged with nitrogen
  2. temperatureheated
  3. temperatureat reflux overnight
  4. custompartitioned between saturated aq. NH4Cl and ethyl acetate (500 ml)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe volatiles were evaporated under reduced pressure
  8. customto give a residue
  9. customThe residue was purified by column chromatography (ISCO, 330 g silica gel column, eluting with 100% hexanes)

Sources & evidence

ORD record
ord-1aa927c2431c4c5e9633d685c2441042
Source dataset
uspto-grants-2015_04
Patent number
US09018381B2

Reaction notes

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