Ethyl bromoacetate → HCID 68918090, compound

HRID 2111643Notes

Reaction equation

HRID 2111643 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[C:7](=[O:12])[N:6]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH:5]2[OH:20].[H-].[Na+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>O1CCCC1>[CH3:11][C:10]1[CH:9]=[C:8]2[C:4](=[CH:3][C:2]=1[CH3:1])[C:5](=[O:20])[N:6]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=1)[CH:7]2[O:12][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 23084577HCID 23084577, compound

Product 1

HCID 68918090HCID 68918090, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5,6-dimethyl-2-(3-fluorophenyl)-3-hydroxyisoindolin-1-one (0.15 g, 0.55 mmol) in anhydrous tetrahydrofuran (5 ml) was added 60% sodium hydride (24 mg, 0.60 mmol), and stirred on ice for 10 minutes. Then, ethyl bromoacetate (67 ml, 0.60 mmol) was added thereto, and stirred at 25° C. overnight. The reaction solution was concentrated under reduced pressure, and water was added to the residue, followed by extracting with ethyl acetate. The extract was washed with saturated brine, dried, and concentrated under reduced pressure to give 0.19 g of 5,6-dimethyl-2-(3-fluorophenyl)-3-ethoxycarbonylmethyloxy-isoindolin-1-one [IUPAC name: ethyl 2-{[2-(3-fluorophenyl)-5,6-dimethyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl]oxy}-acetate].

Workup

  1. stirringstirred at 25° C. overnight
  2. concentrationThe reaction solution was concentrated under reduced pressure, and water
  3. additionwas added to the residue
  4. extractionby extracting with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21a3c04f25f3440c8049299f7aa5599a
Source dataset
uspto-grants-2009_04
Patent number
US07521451B2

Reaction notes

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