Phosphorus tribromide → 3-Bromo-5-(bromomethyl)-2-(2,4-difluorophenoxy)pyridine

HRID 930935Notes

Reaction equation

HRID 930935 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:17]O)[CH:5]=[N:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16].[Br:19]P(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[N:6][CH:5]=[C:4]([CH2:17][Br:19])[CH:3]=1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 86721075(5-Bromo-6-(2,4-difluorophenoxy)pyridin-3-yl)methanol

Product 1

HCID 867210763-Bromo-5-(bromomethyl)-2-(2,4-difluorophenoxy)pyridineYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from Example 311b (0.73 g, 2.309 mmol) in dichloromethane (11.55 mL) under nitrogen was treated dropwise with tribromophosphine (0.218 mL, 2.309 mmol), stirred for one hour at ambient temperature and poured into ice water and the pH was adjusted to pH 9 by addition of solid sodium bicarbonate added portionwise. An emulsion formed that was partially removed by filtration. The aqueous layer was extracted with dichloromethane and the organics were combined, washed with saturated aqueous sodium chloride, dried (Na2SO4) filtered, and concentrated to afford the title compound (0.75 g, 86%).

Workup

  1. additionadded portionwise
  2. customAn emulsion formed
  3. customthat was partially removed by filtration
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c15b383355b6475faa1e7c95d82ea111
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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