Sodium Carbonate → 5'-Chloro-2'-methyl4-trifluoromethyl-biphenyl

HRID 1267108

Reaction equation

HRID 1267108 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH3:9].C([O-])([O-])=O.[Na+].[Na+].[F:16][C:17]([F:28])([F:27])[C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>C1(C)C=CC=CC=1.CO.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>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([CH3:9])=[C:2]([C:21]2[CH:22]=[CH:23][C:18]([C:17]([F:28])([F:27])[F:16])=[CH:19][CH:20]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 6098982-Bromo-4-chloro-1-methylbenzeneHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 185454465'-Chloro-2'-methyl4-trifluoromethyl-biphenylYield 93.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-bromo-4-chloro-toluene (20.5 g) in toluene (100 mL) was added Pd(PPh3)4 (1 g) and the mixture was stirred at room temperature under N2 for 0.25 hours. A 2M solution of Na2CO3 (100 mL) was then added, followed by the dropwise addition of 4-trifluoromethylphenyl boronic acid (19 g) in MeOH (100 mL). The resulting mixture was heated under reflux for 48 hours. The mixture was then cooled to room temperature and the phases were separated. The organic layer was then dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography eluting with petroleum ether/AcOEt (90/10) to give the title compound (25.3 g) as a colorless liquid.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 48 hours
  3. temperatureThe mixture was then cooled to room temperature
  4. customthe phases were separated
  5. dry with materialThe organic layer was then dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was purified by flash chromatography
  9. washeluting with petroleum ether/AcOEt (90/10)

Sources & evidence

ORD record
ord-5008ef1b3ea04cb88930c85a9ab56e0f
Source dataset
uspto-grants-2003_04
Patent number
US06552022B1

Linked notes

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