Phosphorus tribromide → 3-(Bromomethyl)quinoline

HRID 629999Notes

Reaction equation

HRID 629999 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11]O)[CH:2]=1.[Br:13]P(Br)Br>ClCCl>[Br:13][CH2:11][C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 12662983(Quinolin-3-yl)methanol

Product 1

HCID 235103313-(Bromomethyl)quinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Quinolin-3-ylmethanol was dissolved dichloromethane (15 mL) at 0° C. under nitrogen. Tribromophosphane (2.15 mL, 22 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)quinoline, 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-8ffc4ab2fcf34f099aed44bd2ee7c7f1
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

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