Toluene → 2-Bromo-1-[3-(trifluoromethyl)phenyl]ethan-1-one

HRID 229730

Reaction equation

HRID 229730 reaction equation
C1(C)C=CC=CC=1.[F:8][C:9]([F:20])([F:19])[C:10]1[CH:11]=[C:12]([C:16](=[O:18])[CH3:17])[CH:13]=[CH:14][CH:15]=1.C1C=C[NH+]=CC=1.[Br:27][Br-]Br>O>[Br:27][CH2:17][C:16]([C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:9]([F:19])([F:20])[F:8])[CH:11]=1)=[O:18]

Participants

4

Reactant 2

HCID 1140TolueneHCID 676823'-(Trifluoromethyl)acetophenone

Product 1

HCID 27783862-Bromo-1-[3-(trifluoromethyl)phenyl]ethan-1-oneYield 81.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a toluene solution (423 mL) of commercially available 3′-trifluoromethylacetophenone (79.6 g, 0.423 mol) was added pyridinium bromide perbromide (135.4 g, 0.423 mol) under ice cooling and stirred for 5 hours while heating up to room temperature. The reaction liquid was ice cooled again, followed by dropwise adding 400 mL of distilled water to stop reaction and fractionation. A toluene layer was washed with 400 mL of a saturated aqueous solution of sodium bicarbonate, followed by drying with magnesium sulfate anhydride and concentration under reduced pressure and distillation under reduced pressure to obtain an objective compound (92.35 g, 81.7%).

Workup

  1. customThe reaction liquid
  2. temperaturecooled again
  3. customreaction and fractionation
  4. washA toluene layer was washed with 400 mL of a saturated aqueous solution of sodium bicarbonate
  5. dry with materialby drying with magnesium sulfate anhydride and concentration under reduced pressure and distillation under reduced pressure

Sources & evidence

ORD record
ord-1563afc41a58401c95a39af9048a3f05
Source dataset
uspto-grants-2009_07
Patent number
US07563893B2

Linked notes

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