Ethyl bromoacetate → Isoindoline

HRID 2036229Notes

Reaction equation

HRID 2036229 reaction equation
C(OC([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1C1C=C(Cl)C=CC=1O)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].BrCC(OCC)=O>CC(C)=O.O>[CH2:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][NH:8]1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 66654476HCID 66654476, compound

Product 1

HCID 422478Isoindoline

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a mixture of (±)-1-(5-chloro-2-hydroxy-phenyl)-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester (7.47 g, 21.6 mmol, 1.0 eq.) and potassium carbonate anhydrous (4.48 g, 32.4 mmol, 1.5 eq.) in acetone (400 mL), ethyl bromoacetate (2.63 mL, 23.8 mmol, 1.1 eq.) was added. The mixture was stirred at r.t. for 18 hours. The reaction mixture was poured in water (150 mL). The mixture was extracted with AcOEt (2×200 mL). The comb. org. phases were dried over MgSO4 and concentrated in vacuo. The residue was purified by flash master (column: 340 g, flow: 90 mL/min, Heptane to Heptane+50% EtOAc) to yield the title product as an yellow oil.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with AcOEt (2×200 mL)
  3. dry with materialphases were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash master (column: 340 g, flow: 90 mL/min, Heptane to Heptane+50% EtOAc)

Sources & evidence

ORD record
ord-8852223ed67c41cf9bf877c03030bcfa
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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