Sodium Iodide → Acetic acid, 2-(3-bromophenoxy)-, methyl ester

HRID 1979072Notes

Reaction equation

HRID 1979072 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Br[CH2:12][C:13]([O:15][CH3:16])=[O:14].[I-].[Na+]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 115633-BromophenolHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 13827038Acetic acid, 2-(3-bromophenoxy)-, methyl esterYield 80.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 3-bromophenol (17.3 g, 100 mmol) in 30 ml of THF is added at ambient temperature to a 50% solution of sodium hydride dispersed in mineral oil (5 g, 125 mmol) in 50 ml of anhydrous THF. The mixture was stirred at ambient temperature for 30 minutes before successively adding a solution of methyl bromoacetate (10.4 ml, 110 mmol) in 33 ml of anhydrous THF and sodium iodide (3.75 g, 25 mmol). The reaction medium is stirred for 30 minutes at ambient temperature and then treated with 30 ml of water at 0° C. The raw product is purified by chromatography on silica (eluent petroleum ether:ether 100:10). 19.66 g of methyl 3-bromophenoxyacetate is obtained (yield=80%).

Workup

  1. stirringThe reaction medium is stirred for 30 minutes at ambient temperature
  2. customThe raw product is purified by chromatography on silica (eluent petroleum ether:ether 100:10)

Sources & evidence

ORD record
ord-527bca6aad54418ba8d9f2a451407f67
Source dataset
uspto-grants-2001_05
Patent number
US06239284B1

Reaction notes

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