Cesium carbonate → 4'-Fluoro-4-methylbiphenyl-3-amine

HRID 1963986

Reaction equation

HRID 1963986 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)O1.Br[C:18]1[CH:19]=[CH:20][C:21]([CH3:25])=[C:22]([CH:24]=1)[NH2:23].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C:18]2[CH:19]=[CH:20][C:21]([CH3:25])=[C:22]([NH2:23])[CH:24]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27348055-Bromo-o-toluidineHCID 27605932-(4-Fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 463144304'-Fluoro-4-methylbiphenyl-3-amineYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.0 g (22.5 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-fluorobenzene, 1.87 mL (15 mmol) of 5-bromo-2-methylaniline, 1.73 g (1.5 mmol) of tetrakis(triphenyl phosphine)palladium (0), and 7.33 g (15 mmol) of cesium carbonate were heated under reflux for 8 hours in 150 mL of THF. After completion of the reaction, THF was distilled off under reduced pressure, and ethyl acetate was added to separate the solid by filtration. The organic layer was then washed with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled off under reduced pressure. The resulting crude product was separated and purified using silica gel column chromatography, thereby giving 4′-fluoro-4-methylbiphenyl-3-amine (yield: 43%).

Workup

  1. distillationwas distilled off under reduced pressure, and ethyl acetate
  2. additionwas added
  3. customto separate the solid
  4. filtrationby filtration
  5. washThe organic layer was then washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThereafter, the solvent was distilled off under reduced pressure
  8. customThe resulting crude product was separated
  9. custompurified

Sources & evidence

ORD record
ord-06a31f7821b24146988f04d108ea49f6
Source dataset
uspto-grants-2013_04
Patent number
US08415479B2

Linked notes

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