Acetone → 1-Bromo-3-(3-fluoro-2-methyl-phenyl)-propan-2-one

HRID 1963090Notes

Reaction equation

HRID 1963090 reaction equation
[Br:1]Br.[F:3][C:4]1[C:5]([CH3:14])=[C:6]([CH2:10][C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][CH:9]=1.Br.CC(C)=O>C(O)(=O)C>[Br:1][CH2:12][C:11](=[O:13])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([F:3])[C:5]=1[CH3:14]

Participants

6

Reactant 4

HCID 180AcetoneHCID 260Hydrogen BromideHCID 24408BromineHCID 247216491-(3-Fluoro-2-methylphenyl)propan-2-one

Product 1

HCID 866706671-Bromo-3-(3-fluoro-2-methyl-phenyl)-propan-2-oneYield 69.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

Analogously to the procedure described in H. Y. Choi et al., Org. Lett. 5 (2003), 411, a solution of bromine (8.46 g, 52.95 mmol) in acetic acid (12 ml) was added at 0° C. to a solution of 1-(3-fluoro-2-methyl-phenyl)-propan-2-one (4.00 g, 24.07 mmol) in acetic acid (4 ml) and a 33% solution of hydrogen bromide in acetic acid (4 ml). The mixture was warmed to room temperature and stirred for 12 h. Then acetone was added and the mixture was stirred for 24 h. After evaporation under reduced pressure, the residue was extracted several times with DCM. The combined extracts were dried over sodium sulfate and evaporated to dryness. The residue was purified by preparative HPLC to give 4.10 g of the title compound as an oil.

Workup

  1. stirringthe mixture was stirred for 24 h
  2. customAfter evaporation under reduced pressure
  3. extractionthe residue was extracted several times with DCM
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-e995ad2801044255bf33f9df0d108906
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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