Ethyl Acetate → 5-Bromo-2-(4-fluorophenyl)pyridine

HRID 2069311Notes

Reaction equation

HRID 2069311 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][N:13]=1.C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C(O)C.C1(C)C=CC=CC=1.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:18][C:15]1[CH:16]=[CH:17][C:12]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:13][CH:14]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 693532,5-DibromopyridineHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 221807795-Bromo-2-(4-fluorophenyl)pyridine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

22.4 g (160 mmol) of 4-fluoro-benzeneboronic acid, 34 g (153.5 mmol) of 2,5-dibromopyridine and 1.24 g of tetrakis(triphenylphosphine)palladium were dissolved in 240 ml of ethanol and 480 ml of toluene. 480 ml of a 2 N sodium carbonate solution were added and the resulting mixture was heated to 50° C. with stirring for 2 h. After addition of 400 ml of ethyl acetate the mixture was filtered, the phases were separated and the organic phase was washed with a saturated sodium chloride solution, dried and evaporated. The obtained product was purified by column chromatography (silica gel, dichloromethane/heptane 1:1) and preparative HPLC (RP 18). Yield: 12 g.

Workup

  1. filtrationwas filtered
  2. customthe phases were separated
  3. washthe organic phase was washed with a saturated sodium chloride solution
  4. customdried
  5. customevaporated
  6. customThe obtained product was purified by column chromatography (silica gel, dichloromethane/heptane 1:1) and preparative HPLC (RP 18)

Sources & evidence

ORD record
ord-c9bd73f3a92d4a69a03dd60a76c49812
Source dataset
uspto-grants-2012_10
Patent number
US08299102B2

Reaction notes

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