2,4-Dichlorophenol → HCID 682839, compound

HRID 1754924Notes

Reaction equation

HRID 1754924 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].[CH2:16]([O:18][C:19](=[O:24])[C:20](Br)([CH3:22])[CH3:21])[CH3:17].[NH4+].[Cl-]>CN(C)C(=O)C.O>[CH2:16]([O:18][C:19](=[O:24])[C:20]([O:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])([CH3:22])[CH3:21])[CH3:17]

Participants

7

Reactant 4

HCID 84492,4-DichlorophenolHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 25517Ammonium Chloride

Product 1

HCID 682839HCID 682839, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

2,4-Dichlorophenol (448 mg, 2.75 mmol) and K2CO3 (775 mg, 5.61 mmol) were continuously added to 2-bromo-2-methyl-propionic acid ethyl ester (800 mg, 4.10 mmol) in N,N-dimethylacetamide (4 ml) at room temperature. The mixture was stirred at 110° C. for 14 hours, and saturated NH4Cl and H2O were then added, followed by extraction with AcOEt (×2). The organic layers were combined and sequentially washed with H2O and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/AcOEt) to give 2-(2,4-dichloro-phenoxy)-2-methyl-propionic acid ethyl ester (389 mg, 50%).

Workup

  1. extractionfollowed by extraction with AcOEt (×2)
  2. washsequentially washed with H2O and saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane/AcOEt)

Sources & evidence

ORD record
ord-e6abcb44f86642f7a5873078ac36543e
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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