2-(3-Bromophenyl)-1,3-dioxane → 4-(3-[1,3]Dioxan-2-ylphenyl)-1,1,1-trifluoro-4-methylpentan-2-one

HRID 2106025Notes

Reaction equation

HRID 2106025 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]2[O:13][CH2:12][CH2:11][CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.[F:14][C:15]([F:23])([F:22])[C:16](=[O:21])[CH:17]=[C:18]([CH3:20])[CH3:19]>[Cu]I>[O:9]1[CH2:10][CH2:11][CH2:12][O:13][CH:8]1[C:4]1[CH:3]=[C:2]([C:18]([CH3:20])([CH3:19])[CH2:17][C:16](=[O:21])[C:15]([F:23])([F:22])[F:14])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 101058152-(3-Bromophenyl)-1,3-dioxaneHCID 220326911,1,1-Trifluoro-4-methylpent-3-en-2-one

Product 1

HCID 578099664-(3-[1,3]Dioxan-2-ylphenyl)-1,1,1-trifluoro-4-methylpentan-2-one

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

To a solution of the Grignard reagent derived from 2-(3-bromophenyl)-[1,3]dioxane (52.6 mL of 0.25M in THF, 13.1 mmol) at 0° C. was added copper (I) iodide (25 g, 13.1 mmol). After 45 minutes, 1,1,1-trifluoro-4-methylpent-3-en-2-one (2 g, 13.1 mmol) was added and the reaction mixture slowly warmed to room temperature and stirred overnight. The mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride solution, dried with sodium sulfate, and concentrated in vacuo. The residue was triturated with hexanes and filtered. The filtrate was concentrated in vacuo to give 4-(3-[1,3]dioxan-2-ylphenyl)-1,1,1-trifluoro-4-methylpentan-2-one.

Workup

  1. customThe mixture was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with hexanes
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-378125540864487582fd5ce401f22e0b
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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