Potassium Carbonate → [2-[(5-Bromopentyl)oxy]phenoxy]acetic acid methyl ester

HRID 327938Notes

Reaction equation

HRID 327938 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14].Br[CH2:16][C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:20][O:19][C:17](=[O:18])[CH2:16][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 131976012-[(5-Bromopentyl)oxy]phenol

Product 1

HCID 54229658[2-[(5-Bromopentyl)oxy]phenoxy]acetic acid methyl esterYield 66.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.6 g (10 mmol) of 2-[(5-bromopentyl)oxy]phenol, 1.8 g (12 mmol) of methyl bromoacetate, 4.4 g (32 mmol) of anhydrous granular potassium carbonate, and 60 mL of dry acetonitrile was stirred and refluxed for 20 hr. The mixture was cooled and filtered with suction. The solids were washed with ether and the filtrate and washes were combined and concentrated in vacuo. The oily residue was purified by flash chromatography on silica gel, eluting with 3:1 hexane-ether. There was obtained 2.2 g (66.5%) of [2-[(5-bromopentyl)oxy]phenoxy]acetic acid methyl ester as an oil.

Workup

  1. temperaturerefluxed for 20 hr
  2. temperatureThe mixture was cooled
  3. filtrationfiltered with suction
  4. washThe solids were washed with ether
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was purified by flash chromatography on silica gel
  7. washeluting with 3:1 hexane-ether

Sources & evidence

ORD record
ord-687d4e7dd6904f0ab21bf04ed39bbc47
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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