Triphenylphosphine → 5-(Benzyloxy)-2-(bromomethyl)pyridine

HRID 591281Notes

Reaction equation

HRID 591281 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15]O)=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][Br:17])=[N:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 11736050(5-(Benzyloxy)pyridin-2-yl)methanol

Product 1

HCID 797999495-(Benzyloxy)-2-(bromomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 540 mg (2.51 mmol) 5-benzyloxy-2-pyridinemethanol (prepared according to J. Med. Chem. 1977, 20, 1258-1262), 536 mg N-bromo succinimide (3.01 mmol), and 1.2 g polymer bound triphenylphosphine (loading approx. 3 mmol/g, approx. 3.3 mmol) in dichloromethane (40 mL) was stirred overnight at room temperature. All solids were removed by filtration, and the filtrate was washed with aqueous sodium bicarbonate and water, and than concentrated in vacuo. The crude product (540 mg of a slightly pink solid, 79% crude yield) was used without further purification.

Workup

  1. customAll solids were removed by filtration
  2. washthe filtrate was washed with aqueous sodium bicarbonate and water
  3. concentrationthan concentrated in vacuo
  4. customThe crude product (540 mg of a slightly pink solid, 79% crude yield) was used without further purification

Sources & evidence

ORD record
ord-f5186209fbde4ee48bd077373148255b
Source dataset
uspto-grants-2016_01
Patent number
US09238631B2

Reaction notes

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