Carbon tetrabromide → 2-(Bromomethyl)-6-methoxypyridine

HRID 79294Notes

Reaction equation

HRID 79294 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9]O)[CH:6]=[CH:5][CH:4]=1.[Br:11]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:11][CH2:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 12325389(6-Methoxypyridin-2-yl)methanol

Product 1

HCID 100815502-(Bromomethyl)-6-methoxypyridineYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (6-methoxypyridin-2-yl)methanol (3.36 g, 24.1 mmol) in DCM (30 mL) was added perbromomethane (12.0 g, 36.2 mmol) and triphenylphosphine (9.50 g, 36.2 mmol). The reaction mixture was stirred for 1 hour, concentrated and silica gel chromatography (EtOAc/Hexane 1:5) to provide the desired product (4.23 g).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-329eca199b4c468c9768351cf32f991a
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…