Carbon tetrabromide → 5-(Bromomethyl)-2-phenoxypyridine

HRID 594318Notes

Reaction equation

HRID 594318 reaction equation
[O:1]([C:8]1[N:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:17].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:17][CH2:14][C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:13][CH:12]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 2776502(6-Phenoxypyridin-3-yl)methanol

Product 1

HCID 690824005-(Bromomethyl)-2-phenoxypyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of commercially available (6-phenoxypyridin-3-yl)methanol (150 mg; 0.74 mmol) in anh. DCM (6 ml) was treated at rt with CBr4 (247 mg; 0.74 mmol), and with PPh3 (195 mg; 0.74 mmol). The resulting mixture was further stirred at rt, under nitrogen, for 15 h. Concentration to dryness under reduced pressure, and subsequent purification by FC (DCM) afforded 5-(bromomethyl)-2-phenoxypyridine as a pale yellow oil which was directly used for the next reaction. LC-MS (conditions A): tR=0.84 min.; [M+H]+: 263.98 g/mol.

Workup

  1. concentrationConcentration to dryness
  2. customunder reduced pressure, and subsequent purification by FC (DCM)

Sources & evidence

ORD record
ord-ff85c6f7590d444ab2af8e936622756b
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

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