Phosphorus tribromide → 3-(Bromomethyl)-2-fluoropyridine

HRID 576975Notes

Reaction equation

HRID 576975 reaction equation
[F:1][C:2]1[C:7]([CH2:8]O)=[CH:6][CH:5]=[CH:4][N:3]=1.P(Br)(Br)[Br:11]>ClCCl>[Br:11][CH2:8][C:7]1[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 147614612-Fluoro-3-(hydroxymethyl)pyridine

Product 1

HCID 230708853-(Bromomethyl)-2-fluoropyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude (2-fluoropyridin-3-yl)methanol was dissolved in dichloromethane (30 mL) at 0° C. under nitrogen. Phosphorus tribromide (4.2 mL, 42 mmol) was added dropwise. The resulting mixture was stirred at room temperature overnight. The reaction was quenched by addition of 10% NaHCO3 solution (5 mL). After 10 minutes, Na2SO4 (30 g) was added. The solvent was filtered and evaporated to provide 3-(bromomethyl)-2-fluoropyridine, which was used without further purification.

Workup

  1. customThe reaction was quenched by addition of 10% NaHCO3 solution (5 mL)
  2. waitAfter 10 minutes
  3. additionNa2SO4 (30 g) was added
  4. filtrationThe solvent was filtered
  5. customevaporated

Sources & evidence

ORD record
ord-31276344b49c4386bb1cc7a66c91a9f9
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Reaction notes

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