Carbon tetrabromide → 3-Bromo-5-(bromomethyl)pyridine

HRID 712588Notes

Reaction equation

HRID 712588 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][Br:30])[CH:3]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 149329483-Bromo-5-(bromomethyl)pyridineYield 91.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of (5-bromo-pyridin-3-yl)-methanol (5.0 g, 26.6 mmol) and triphenylphosphine (8.4 g, 31.9 mmol) in DCM (130 mL) is added carbon tetrabromide (13.2 g, 39.9 mmol). The resulting mixture is stirred at 0° C. for 10 min. The mixture is concentrated and purified by silica gel column (0-40% EtOAc in heptane) to afford the title compound (6.1 g).

Workup

  1. concentrationThe mixture is concentrated
  2. custompurified by silica gel column (0-40% EtOAc in heptane)

Sources & evidence

ORD record
ord-5a60ea52cee24a2ba758cba0fb909228
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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