Carbon tetrabromide → 2-Bromo-5-bromomethylpyridine

HRID 2062121Notes

Reaction equation

HRID 2062121 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][Br:30])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 64212496-Bromo-3-pyridinemethanol

Product 1

HCID 64246602-Bromo-5-bromomethylpyridineYield 74.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.91 g (6-bromo-pyridin-3-yl)-methanol in 10 mL of dichloromethane was added 1.88 g of triphenyl phosphine and 2.38 g of carbon tetrabromide. This mixture was stirred at room temperature for 3 hours. It was then concentrated on silica gel, eluted with heptane/ethyl acetate to provide 0.91 g of 2-bromo-5-bromomethyl-pyridine.

Workup

  1. concentrationIt was then concentrated on silica gel
  2. washeluted with heptane/ethyl acetate

Sources & evidence

ORD record
ord-305e809059cf44d2a3bdcbedcccac550
Source dataset
uspto-grants-2012_10
Patent number
US08283479B2

Reaction notes

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