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

HRID 1073206Notes

Reaction equation

HRID 1073206 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.C(C1C=CC=CC=1)(=O)C>C(O)(=O)C>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[C:9](=[O:11])[CH2:10][Br:14]

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 24408BromineHCID 676823'-(Trifluoromethyl)acetophenone

Product 1

HCID 27783862-Bromo-1-[3-(trifluoromethyl)phenyl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

m-(Trifluoromethyl)acetophenone (10 g, 0.054 mol) was dissolved in 100 ml acetic acid. Bromine (9.1 g, 0.057 mol) was separately dissolved in 20 ml acetic acid and added portionwise over 0.5 hours to the acetophenone solution. The mixture was stirred for 15 hours, poured onto 150 g ice and extracted with 300 ml ether. The organic layer was washed 1×300 ml H2O, 1×300 ml saturated NaCl, dried (MgSO4) and evaporated to yield title product as a pale yellow liquid.

Workup

  1. extractionextracted with 300 ml ether
  2. washThe organic layer was washed 1×300 ml H2O, 1×300 ml saturated NaCl
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-aa1689af12be489f9f9e86dba5a79722
Source dataset
uspto-grants-1990_11
Patent number
US04968707

Reaction notes

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