Sodium Iodide → HCID 86718431, compound

HRID 571348Notes

Reaction equation

HRID 571348 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[CH:22]=[CH:21][C:11]([O:12][C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17]Cl)=[O:15])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[I-:25].[Na+]>CC(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[CH:22]=[CH:21][C:11]([O:12][C:13]([CH3:20])([CH3:19])[C:14]([O:16][CH2:17][I:25])=[O:15])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 57586167Chloromethyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate

Product 1

HCID 86718431HCID 86718431, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Chloromethyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate 1 (3.0 g, 8.2 mmol) was dissolved in acetone (50 mL) at room temperature. Sodium iodide (2.4 g, 16.3 mmol, 2 eq) was added and the clear solution was stirred 10 min at room temperature, then heated to 50° C. for 6 hr. The mixture was cooled to room temperature, diluted with ethyl acetate (200 mL) and filtered. The filtrate was washed with water (3×10 mL) and brine then dried over sodium sulfate. The drying agent was filtered off and the solution was concentrated by rotary evaporation to leave iodomethyl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate 2 as a thick, yellow oil (3.7 g, 99% yield) that was used directly in the next reaction without further purification. 1H-NMR (CDCl3) δ 7.74 (d, 2 H), 7.71 (d, 2 H), 7.45 (d, 2 H), 6.85 (d, 2 H), 5.97, (s, 2 H), 1.67 (s, 6 H) ppm.

Workup

  1. temperatureheated to 50° C. for 6 hr
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. washThe filtrate was washed with water (3×10 mL) and brine
  5. dry with materialthen dried over sodium sulfate
  6. filtrationThe drying agent was filtered off
  7. concentrationthe solution was concentrated by rotary evaporation

Sources & evidence

ORD record
ord-e294d856d44147109ba85def42eb04c9
Source dataset
uspto-grants-2015_05
Patent number
US09024069B2

Reaction notes

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