Carbon tetrabromide → 2-(Bromomethyl)-6-(methoxymethyl)pyridine

HRID 723435Notes

Reaction equation

HRID 723435 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[N:9]=[C:8]([CH2:10]O)[CH:7]=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:32]>ClCCl>[Br:32][CH2:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:3][O:2][CH3:1])[N:9]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21874550[6-(Methoxymethyl)pyridin-2-yl]methanol

Product 1

HCID 218745862-(Bromomethyl)-6-(methoxymethyl)pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6-methoxymethyl-2-pyridinemethanol (860 mg, 5.64 mmol) and triphenylphosphine (1.78 g, 6.77 mmol) in dichloromethane (40 mL) at 0° C. was treated portion wise with CBr4 (2.80 g, 8.43 mmol), stirred for 1 h, concentrated in vacuo and purified by chromatography [SiO2; isohexane:EtOAc (3:1)] to give the title compound (1.20 g, 99%) as a colourless oil; NMR δH (400 MHz, CDCl3) 7.71 (1H, t, J 8.0 Hz), 7.35 (2H, d, J 8.0 Hz), 4.58 (2H, s) and 4.54 (2H, s).

Workup

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

Sources & evidence

ORD record
ord-d8abded127ea48849a3f2983c2d5409a
Source dataset
uspto-grants-2006_11
Patent number
US07141575B2

Reaction notes

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