Ethyl bromoacetate → HCID 53821086, compound

HRID 581986Notes

Reaction equation

HRID 581986 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[CH:7][C:8]=1[Br:9].[H-].[Na+].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[Br:9])[O:10][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 3479554-Bromo-3-methoxyphenol

Product 1

HCID 53821086HCID 53821086, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methoxy-4-bromophenol D8 (6.95 g, 34 mmoles) in dry dimethylformamide (100 ml) at 0° C. was treated with sodium hydride (80% dispersion in oil) (1.13 g, 37 mmoles). After 30 mins ethyl bromoacetate (3.8 ml, 34 mmoles) was added and the mixture allowed to warm to room temperature over 1 hr. The mixture was concentrated in vacuo and the residue partitioned between water and diethyl ether. The organic layer was washed several times with water and then dried (Na2SO4) and evaporated to dryness. Flash chromatography on TLC silica gel eluting with dichloromethane gave the title compound (D9) (7.43 g, 75%)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue partitioned between water and diethyl ether
  3. washThe organic layer was washed several times with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-aa615a39fd1a42afaed34ff1e82f0fba
Source dataset
uspto-grants-1999_07
Patent number
US05922733

Reaction notes

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