2,5-Dibromopyridine → 5-Bromo-2-(2,6-difluorobenzyl)pyridine

HRID 1454975Notes

Reaction equation

HRID 1454975 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Br-].[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:12]=1[CH2:13][Zn+]>C1COCC1.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:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:13][C:12]2[C:11]([F:10])=[CH:18][CH:17]=[CH:16][C:15]=2[F:19])=[N:3][CH:4]=1

Participants

5

Reactant 2

HCID 693532,5-DibromopyridineHCID 178505728HCID 178505728, compound

Product 1

HCID 575312355-Bromo-2-(2,6-difluorobenzyl)pyridine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,5-dibromopyridine (10 g) in THF was added Tetrakis (2.2 g) and 2,6-difluorobenzylzinc bromide (126 mL, 63 mmol). The reaction was heated to reflux until reaction was complete by TLC. The reaction was cooled to room temperature, filtered through celite, and concentrated in vacuo. The title compound was purified by silica gel (Hexanes/methylene chloride).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux until reaction
  3. filtrationfiltered through celite
  4. concentrationconcentrated in vacuo
  5. customThe title compound was purified by silica gel (Hexanes/methylene chloride)

Sources & evidence

ORD record
ord-32d5028e2bcb45509fcf0f3760b78004
Source dataset
uspto-grants-2009_01
Patent number
US07482345B2

Reaction notes

Loading…