Carbon tetrabromide → 2-Allyloxymethyl-6-bromomethylpyridine

HRID 271279

Reaction equation

HRID 271279 reaction equation
[CH2:1]([O:4][CH2:5][C:6]1[N:11]=[C:10]([CH2:12]O)[CH:9]=[CH:8][CH:7]=1)[CH:2]=[CH2:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:34]>ClCCl>[CH2:1]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([CH2:12][Br:34])[N:11]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 218747256-Allyloxymethyl-2-Pyridinemethanol

Product 1

HCID 218745842-Allyloxymethyl-6-bromomethylpyridineYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-allyloxymethylpyridine-2-methanol (1.56 g, 8.72 mmol) and triphenylphosphine (2.74 g, 10.5 mmol) in dichloromethane (40 mL) at 0° C. was treated portionwise with CBr4 (4.34 g, 13.1 mmol), stirred for 1 h, concentrated in vacuo and purified by chromatography [SiO2; isohexane:EtOAc (3:1)] to give the title compound (1.99 g, 94%) as a colourless oil: NMR δH (400 MHz, CDCl3) 7.71 (1H, t, J 7.5 Hz), 7.40 (1H, d, J 7.5 Hz), 7.34 (1H, d, J 7.5 Hz), 6.03-5.93 (1H, m), 5.37-5.32 (1H, m), 5.26-5.22 (1H, m), 4.64 (2H, s), 4.54 (2H, s) and 4.14-4.12 (2H, m).

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified by chromatography [SiO2; isohexane:EtOAc (3:1)]

Sources & evidence

ORD record
ord-3f8ee51236054a3f8f3438ff43722d6b
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Linked notes

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