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

HRID 474606Notes

Reaction equation

HRID 474606 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][CH:8]=2)=[CH:4][C:3]=1[C:17]([F:20])([F:19])[F:18].P(Br)(Br)[Br:22].C([O-])(O)=O.[Na+]>C(OCC)C>[Br:22][CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:15]=[CH:16][C:2]([Cl:1])=[C:3]([C:17]([F:20])([F:19])[F:18])[CH:4]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 66825563(4-(4-Chloro-3-(trifluoromethyl)phenoxy)phenyl)methanol

Product 1

HCID 677759764-(4-(Bromomethyl)phenoxy)-1-chloro-2-(trifluoromethyl)benzeneYield 53%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the solution of (4-(4-chloro-3-(trifluoromethyl)phenoxy)phenyl)methanol (4.5 g, 14.87 mmol) in Diethyl ether (100 mL) was added PBr3 (1.402 mL, 14.87 mmol) dropwise at 0° C. The mixture was stirred at room temperature for 5 h. The mixture was poured into ice water and neutralized with sat. NaHCO3 solution to pH ˜7, then extracted with Et2O. The organic was dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound (3.2 g, 7.88 mmol, 53.0% yield) as a light yellow solid. LCMS: rt=2.01 min, [M+H+]=365, 367.

Workup

  1. extractionextracted with Et2O
  2. dry with materialThe organic was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3154fecf16154d8eaa05a2644d597cdd
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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