Ethyl bromoacetate → HCID 59235356, compound

HRID 2174342Notes

Reaction equation

HRID 2174342 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:16])=[C:6]([CH:15]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C)C=O.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:16])=[C:6]([CH:15]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 574237514-((5-Bromo-2-chlorophenyl)methyl)phenol

Product 1

HCID 59235356HCID 59235356, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred suspension of 4-(5-bromo-2-chlorobenzyl)phenol (5.0 g, 16.8 mmol) in N,N-dimethylformamide (20 mL) and cesium carbonate (11.0 g, 33.6 mmol) was added ethyl 2-bromoacetate (2.8 mL, 25.2 mmol). The mixture was stirred overnight at 80° C. The solution was diluted with water, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with brine prior to drying over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography to give 5.0 g of white solid (78% yield).

Workup

  1. extractionthe aqueous layer was extracted with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialto drying over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-10196f53975340b29760731ff05a6687
Source dataset
uspto-grants-2015_06
Patent number
US09061060B2

Reaction notes

Loading…