Phosphorus oxychloride → 5-Bromo-2-chloro-3-(trifluoromethyl)pyridine

HRID 1820984Notes

Reaction equation

HRID 1820984 reaction equation
O[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517592HCID 178517592, compound

Product 1

HCID 218363025-Bromo-2-chloro-3-(trifluoromethyl)pyridine

Procedure

A mixture of 1.83 g (7.6 mmol) of 2-hydroxy-3-trifluoromethyl-5-bromopyridine (from Step A) in 15 mL of POCl3 was heated at reflux for 3 h. The mixture was cooled and poured onto 200 g of ice. The resulting mixture was extracted with 200 mL of CH2Cl2. The extract was dried and concentrated. Chromatography on a Biotage 40 M cartridge using hexanes as the eluant afforded 1.11 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 8.14 (d, J=2.0, 1H), 8.64 (d, J=2.0, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureThe mixture was cooled
  4. extractionThe resulting mixture was extracted with 200 mL of CH2Cl2
  5. customThe extract was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b1ecc95fa2144ffd9d5c1a7a95a624fa
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

Loading…