Sodium hydride → HCID 58197057, compound

HRID 1503410Notes

Reaction equation

HRID 1503410 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20]Br.[H-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:20][C:15]4[C:14](=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:13]3)[C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66665o-Bis(bromomethyl)benzeneHCID 1397781-Indanone, 6-bromo-

Product 1

HCID 58197057HCID 58197057, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-bromo-indan-1-one (1.05 g, 5 mmol), 1,2-bis(bromomethyl)benzene (1.31 g, 5 mmol) in THF (50 mL) was added NaH (240 mg, 10 mmol) at room temperature, the mixture was refluxed for 2 hours. The mixture was quenched with water, concentrated, then extracted with DCM, washed with brine, dried over Na2SO4, concentrated to 6-bromo-1′,3′-dihydro-2,2′-spirobi[inden]-1(3H)-one (1.8 g, 33%).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customThe mixture was quenched with water
  3. concentrationconcentrated
  4. extractionextracted with DCM
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to 6-bromo-1′,3′-dihydro-2,2′-spirobi[inden]-1(3H)-one (1.8 g, 33%)

Sources & evidence

ORD record
ord-1185c271ceed4d3a8a51e97e428f848b
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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