Sodium Carbonate → 2-Bromo-4'-(trifluoromethyl)-1,1'-biphenyl

HRID 382117Notes

Reaction equation

HRID 382117 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.[F:9][C:10]([F:21])([F:20])[C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>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:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:14]1[CH:15]=[CH:16][C:11]([C:10]([F:21])([F:20])[F:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 114151-Bromo-2-iodobenzeneHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 120407262-Bromo-4'-(trifluoromethyl)-1,1'-biphenylYield 67.1%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
85 °C

Procedure

An oven dried Schlenk tube was evacuated and backfilled with argon and charged with tetrakis(triphenylphosphine)palladium (289 mg, 0.25 mmol, 5.0 mol %), 2-bromoiodobenzene (0.83 mL, 6.50 mmol), 4-(trifluoromethyl)phenylboronic acid (950 mg, 5.0 mmol), and sodium carbonate (2.86 g, 27.0 mmol). The tube was evacuated and backfilled with argon. To the tube was added (degassed) dimethoxyethane (45 mL), ethanol (2 mL), and water (15 mL) through a rubber septum. The reaction mixture was heated to 85° C. with stirring for 32 hours. The reaction mixture was then diluted with 2:1 hexane/ethyl acetate (100 mL) and poured into a separatory funnel. The mixture was washed with water (80 mL), and brine (80 mL). The organic layer was dried over anhydrous sodium sulfate, decanted, and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel to afford 1.01 g (67%) of the product.

Workup

  1. customAn oven dried Schlenk tube
  2. customwas evacuated
  3. customThe tube was evacuated
  4. additionTo the tube was added (degassed) dimethoxyethane (45 mL), ethanol (2 mL), and water (15 mL) through a rubber septum
  5. additionThe reaction mixture was then diluted with 2:1 hexane/ethyl acetate (100 mL)
  6. additionpoured into a separatory funnel
  7. washThe mixture was washed with water (80 mL), and brine (80 mL)
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. customdecanted
  10. concentrationconcentrated in vacuo
  11. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-8c498b6a9d8947b982d42db22eb761c3
Source dataset
uspto-grants-2001_10
Patent number
US06307087B1

Reaction notes

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