Sodium hydride → 6-bromo-1',3'-dihydrospiro[indene-2,2'-phenalen]-1(3H)-one

HRID 1503407Notes

Reaction equation

HRID 1503407 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[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[CH2:24]Br)[CH:17]=[CH:16][CH:15]=1.[H-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([C:8]2=[O:11])[CH2:24][C:22]2[C:23]4[C:18]([CH:19]=[CH:20][CH:21]=2)=[CH:17][CH:16]=[CH:15][C:14]=4[CH2:13]3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1397781-Indanone, 6-bromo-HCID 2912081,8-Bis(bromomethyl)naphthalene

Product 1

HCID 581970446-bromo-1',3'-dihydrospiro[indene-2,2'-phenalen]-1(3H)-oneYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-bromo-2,3-dihydro-1H-inden-1-one (400 mg, 1.9 mmol) and 1,8-bis(bromomethyl)naphthalene (596 mg, 1.9 mmol) in THF (20 mL) was added NaH (152 mg, 3.8 mmol) at room temperature, the mixture was heated under reflux for 2 h. The mixture was quenched with water, concentrated, then extracted with CH2Cl2, washed with brine, dried over Na2SO4 and concentrated to give 6-bromo-1′,3′-dihydrospiro[indene-2,2′-phenalen]-1(3H)-one (386 mg, 56%). 1H-NMR (CDCl3): 2.79 (d, 2H), 3.50 (d, 2H), 7.12 (m, 1H), 7.18 (m, 2H), 7.36 (m, 2H), 7.60 (m, 1H), 7.71 (m, 1H), 7.92 (m, 1H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. customThe mixture was quenched with water
  4. concentrationconcentrated
  5. extractionextracted with CH2Cl2
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6f3deb2024cb4762ac6a581c9b7bee52
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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