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

HRID 926844Notes

Reaction equation

HRID 926844 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([C:9](=[O:11])[CH3:10])[CH:6]=[CH:7][CH:8]=1.[Br:14]Br>CCOCC>[Br:14][CH2:10][C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=1)=[O:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 676823'-(Trifluoromethyl)acetophenone

Product 1

HCID 27783862-Bromo-1-[3-(trifluoromethyl)phenyl]ethan-1-oneYield 73.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Into a 250-mL round bottom flask, was placed a solution of 1-(3-(trifluoromethyl)phenyl)ethanone (5 g, 26.57 mmol, 1.00 equiv) in ether (80 mL). To this was added dropwise a solution of Br2 (4.26 g, 26.66 mmol, 1.00 equiv) in ether (20 mL) with stirring over 1 hr and the resulting solution was stirred an additional 1 h at room temperature. The mixture was washed with 2×30 mL of NaHSO3 and 1×30 mL of brine, then dried over anhydrous sodium sulfate and concentrated under vacuum to give 5.2 g (crude) of 2-bromo-1-(3-(trifluoromethyl)phenyl)ethanone as yellow oil.

Workup

  1. customInto a 250-mL round bottom flask, was placed
  2. stirringthe resulting solution was stirred an additional 1 h at room temperature
  3. washThe mixture was washed with 2×30 mL of NaHSO3 and 1×30 mL of brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f4629ff1ca7c45da873dc951580b1240
Source dataset
uspto-grants-2016_03
Patent number
US09289430B2

Reaction notes

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