1-Indanone, 4-bromo- → HCID 117665512, compound

HRID 2170737Notes

Reaction equation

HRID 2170737 reaction equation
C([N-]C(C)C)(C)C.[Li+].[Br:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][CH2:13][C:14]2=[O:19].Br[CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1>C1COCC1>[Br:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][CH:13]([CH2:21][C:22]1[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=1)[C:14]2=[O:19]

Participants

5

Reactant 3

HCID 987131-Indanone, 4-bromo-HCID 256687Methyl 4-(bromomethyl)benzoateHCID 2724682Lithium diisopropylamide

Product 1

HCID 117665512HCID 117665512, compoundYield 4.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium diisopropylamide (2.0 M in THF, 2.5 mL, 5.0 mmol) was added to a solution of 4-bromo-2,3-dihydro-1H-inden-1-one (4-bromo-1-indanone, 960 mg, 4.55 mmol) in THF (9.1 mL) at −78° C. After 1 h at −78° C., a solution of methyl 4-(bromomethyl)benzoate (1.25 g, 5.46 mmol) in THF (5 mL) was added via cannula. The reaction mixture was allowed to warm to room temperature naturally. After stirring at room temperature overnight, the reaction was quenched with saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated. The resulting crude residue was purified by combiflash (330 g column, hexanes→30% EtOAc/hexanes, gradient) to afford 72 mg (4%) of methyl 4-((4-bromo-1-oxo-2,3-dihydro-1H-inden-2-yl)methyl)benzoate.

Workup

  1. customthe reaction was quenched with saturated aqueous NH4Cl (50 mL)
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude residue was purified by combiflash (330 g column, hexanes→30% EtOAc/hexanes, gradient)

Sources & evidence

ORD record
ord-f98460ab604d41f8b0d0177e7774ddf8
Source dataset
uspto-grants-2015_06
Patent number
US09051294B2

Reaction notes

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