Ethyl bromoacetate → Acetic acid, (2-iodophenoxy)-, ethyl ester

HRID 2202656Notes

Reaction equation

HRID 2202656 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>CC#N>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 107842-IodophenolHCID 11430Potassium Carbonate

Product 1

HCID 11808921Acetic acid, (2-iodophenoxy)-, ethyl esterYield 79%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-iodophenol (1 g, 4.55 mmol) in CH3CN (20 mL) was added K2CO3 (0.93 g, 6.83 mmol) and ethyl 2-bromoacetate (0.835 g, 5.0 mmol). The reaction mixture was stirred at reflux for 2 h, cooled to room temperature, extracted with EtOAc, washed with brine, dried over sodium sulfate and concentrated. The crude product was used in the next step without further purification. (1.1 g, yield 79%) MS (ESI+) e/z: 307.1 [M+1]+.

Workup

  1. temperatureat reflux for 2 h
  2. extractionextracted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-d1058cef8dfb4de7bb88da395c740b44
Source dataset
uspto-grants-2016_06
Patent number
US09365555B2

Reaction notes

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