Phosphorus tribromide → 2-(Bromomethyl)-4-(phenyloxy)-1-(trifluoromethyl)benzene

HRID 1946401Notes

Reaction equation

HRID 1946401 reaction equation
[C:1]1([O:7][C:8]2[CH:9]=[CH:10][C:11]([C:16]([F:19])([F:18])[F:17])=[C:12]([CH2:14]O)[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:21].C(=O)(O)[O-].[Na+]>ClCCl.O>[Br:21][CH2:14][C:12]1[CH:13]=[C:8]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=[CH:10][C:11]=1[C:16]([F:19])([F:18])[F:17]

Participants

6

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 66770967[5-(Phenyloxy)-2-(trifluoromethyl)phenyl]methanol

Product 1

HCID 667707242-(Bromomethyl)-4-(phenyloxy)-1-(trifluoromethyl)benzeneYield 69.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-5 °C

Procedure

[5-(phenyloxy)-2-(trifluoromethyl)phenyl]methanol (0.493 g, 1.84 mmol) in dichloromethane (12 ml) under nitrogen was stirred and cooled to −5° C. A solution of phosphorus tribromide (173 μl, 1.84 mmol) in DCM (3.5 ml) was added dropwise over about 2 min. The solution was then allowed to warm to room temperature and left to stand overnight. The solution was cooled to 4° C. and stirred well as saturated aqueous sodium bicarbonate (11 ml) was added in portions over 2 min. The biphasic mixture was stirred for a further 20 min. The mixture was diluted with water and DCM. The phases were separated using a hydrophobic frit and the aqueous phase washed with DCM. The combined organic extracts were stored in a freezer over the weekend and the DCM solution decanted off from crystals of ice. The organic phase was further dried (MgSO4), filtered and the solvent removed in vacuo to leave crude 2-(bromomethyl)-4-(phenyloxy)-1-(trifluoromethyl)benzene as a colourless oil (0.425 g).

Workup

  1. temperatureto warm to room temperature
  2. waitleft
  3. temperatureThe solution was cooled to 4° C.
  4. additionwas added in portions over 2 min
  5. customThe phases were separated
  6. washthe aqueous phase washed with DCM
  7. customthe DCM solution decanted off from crystals of ice
  8. dry with materialThe organic phase was further dried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ed38c72a2f274fe59143cc8971372b1d
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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