Sodium Iodide → HCID 59775200, compound

HRID 1361052Notes

Reaction equation

HRID 1361052 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH2:5]Br)[CH3:2].[F:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC(C)=O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:7])=[CH:11][C:10]=1[CH3:16]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 27373944-Fluoro-3-methylphenol

Product 1

HCID 59775200HCID 59775200, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
63 °C

Procedure

To a solution of Bromo-acetic acid ethyl ester (1.3 g, 7.1 mmol) and 4-Fluoro-3-methyl-phenol (1.0 g, 7.1 mmol) in 10 mL acetone was added K2CO3 (979 mg, 7.1 mmol) and NaI (7.1 mg, 0.047 mmol) at 25° C. The reaction mixture was stirred for 3 h at 63° C. and the temperature was slowly reduced to room temperature over a period of 30 min. Evaporation of solvent left the crude from which the product was isolated by Flash column chromatography eluting with 0% to 10% ethyl acetate/hexane to give the title compound, 1.1 g, as a light yellow oil.

Workup

  1. waitthe temperature was slowly reduced to room temperature over a period of 30 min
  2. customEvaporation of solvent
  3. waitleft the crude from which the product
  4. customwas isolated by Flash column chromatography
  5. washeluting with 0% to 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-60d4e7615e5d442caaca9700dec54ddc
Source dataset
uspto-grants-2011_02
Patent number
US07879911B2

Reaction notes

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