Ethyl bromoacetate → Ethyl [(2,3-dimethylphenyl)oxy]acetate

HRID 2175226Notes

Reaction equation

HRID 2175226 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:9].Br[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 106872,3-DimethylphenolHCID 10796Cesium carbonate

Product 1

HCID 17065225Ethyl [(2,3-dimethylphenyl)oxy]acetateYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,3-dimethylphenol (1.0 g, 8.19 mmol), ethyl bromoacetate (1.0 mL, 9.0 mmol) and cesium carbonate (2.67 g, 8.19 mmol) in DMF (10 mL) was stirred at 80° C. for 16 h. After this time, the reaction mixture was partitioned between EtOAc and water. The organic layer was washed with water and brine, dried and concentrated in vacuo to afford the title compound (1.7 g, 100% yield). LCMS, [M+Na]+=231.0.

Workup

  1. customAfter this time, the reaction mixture was partitioned between EtOAc and water
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1c90c4a7e41446c1a2644357b5cbedb8
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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