Carbon tetrabromide → 5-Bromo-2-(bromomethyl)pyridine

HRID 1468817Notes

Reaction equation

HRID 1468817 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8]O)=[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]>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][Br:30])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 5200169(5-Bromopyridin-2-yl)methanol

Product 1

HCID 234380625-Bromo-2-(bromomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-Bromo-2-hydroxymethylpyridine (1 g, 5.32 mmol) was dissolved in dichloromethane (26.6 ml) and cooled to 0° C. Triphenylphosphine (1.604 g, 6.12 mmol) was added followed by carbon tetrabromide (2.028 g, 6.12 mmol) which caused the reaction to become yellow and heterogeneous. After 48 h, the mixture was concentrated by half and directly purified by silica gel column chromatography (0-37%, EtOAc-hexanes) to yield the title compound. 1H NMR (500 MHz, CDCl3) δ 8.64 (t, J 2.7 Hz, 1H), 7.82 (m, 1H), 7.35 (dd, J 7.8 & 3.1 Hz, 1H), 4.51 (s, 2H).

Workup

  1. customthe reaction
  2. concentrationthe mixture was concentrated by half
  3. customdirectly purified by silica gel column chromatography (0-37%, EtOAc-hexanes)

Sources & evidence

ORD record
ord-ec941b6501af424fb430545a4dbb26bb
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

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