Ethyl bromoacetate → HCID 67081820, compound

HRID 2273553Notes

Reaction equation

HRID 2273553 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:10])[CH:6]=[C:7]([OH:9])[CH:8]=1.Br[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[H-].[Na+]>CN1CCCC1=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:6]=[C:5]([O:10][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 71648Flamenol

Product 1

HCID 67081820HCID 67081820, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

5.0 g (35.7 mmol) of 5-methoxybenzene-1,3-diol and then, after 10 minutes, 8.7 ml (78.5 mmol) of ethyl 2-bromoacetate are added to the suspension of 3.1 g (71.4 mmol) of sodium hydride (60% dispersion in oil) in 180 ml of 1-methyl-2-pyrrolidinone under argon. The mixture is stirred at ambient temperature for 3 hours. The reaction medium is diluted with ethyl acetate and washed with a saturated aqueous solution of potassium hydrogen sulphate and a saturated solution of sodium chloride and dried over sodium sulphate then concentrated to dryness. The crude product is purified by chromatography on silica gel (dichloromethane/ethyl acetate=95/5). 5.9 g (53%) of a colourless gum are obtained.

Workup

  1. washwashed with a saturated aqueous solution of potassium hydrogen sulphate
  2. dry with materiala saturated solution of sodium chloride and dried over sodium sulphate
  3. concentrationthen concentrated to dryness
  4. customThe crude product is purified by chromatography on silica gel (dichloromethane/ethyl acetate=95/5)

Sources & evidence

ORD record
ord-360dff1a4ed043e9b665fc5ae1228ae3
Source dataset
uspto-grants-2015_09
Patent number
US09120819B2

Reaction notes

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