Water → 5-(Bromomethyl)-2,3-dichloropyridine

HRID 2089111Notes

Reaction equation

HRID 2089111 reaction equation
[Br:1]P(Br)Br.[Cl:5][C:6]1[CH:7]=[C:8]([CH2:13]O)[CH:9]=[N:10][C:11]=1[Cl:12].O>ClCCl>[Br:1][CH2:13][C:8]1[CH:7]=[C:6]([Cl:5])[C:11]([Cl:12])=[N:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 21882961(5,6-Dichloropyridin-3-yl)methanol

Product 1

HCID 219623285-(Bromomethyl)-2,3-dichloropyridineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.0 mL of tribromophosphine was added to 3.0 g of (5,6-dichloropyridin-3-yl)methanol (16.9 mmol) dissolved in 60 mL of dichloromethane, and stirred at room temperature for 2 hours. 30 mL of water was added dropwise thereto, and the organic layer was separated. The organic layer was washed with saturated sodium bicarbonate, and dried over magnesium sulfate. Then, the organic layer was concentrated under reduced pressure to obtain 3.66 g of 5-(bromomethyl)-2,3-dichloropyridine (yield 90%).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with saturated sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. concentrationThen, the organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8a3bab9ba8454e86b99b10a147238ac9
Source dataset
uspto-grants-2013_05
Patent number
US08436022B2

Reaction notes

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