Sodium hydride → 6'-bromo-5,7,8,9-tetrahydrospiro[benzo[7]annulene-6,2'-inden]-1'(3'H)-one

HRID 1503394Notes

Reaction equation

HRID 1503394 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][CH2:21][CH2:22]Br.[H-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([CH2:22][CH2:21][CH2:20][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[CH2:13]3)[C:8]2=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1397781-Indanone, 6-bromo-HCID 202086332-(3-Bromopropyl)benzyl bromide

Product 1

HCID 581972976'-bromo-5,7,8,9-tetrahydrospiro[benzo[7]annulene-6,2'-inden]-1'(3'H)-oneYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-bromo-2,3-dihydro-1H-inden-1-one (1.2 g, 5.71 mmol) and 1-(bromomethyl)-2-(3-bromopropyl)benzene (1.66 g, 5.71 mmol) in THF (40 mL) was added NaH (457 mg, 60%, 11.42 mmol) at room temperature. The mixture was refluxes for 2 h. The mixture was quenched with water and extracted with EtOAc. The organic layer was dried and concentrated to give the residue, which was purified by column chromatography to give 6′-bromo-5,7,8,9-tetrahydrospiro[benzo[7]annulene-6,2′-inden]-1′(3′H)-one (420 mg, 22%).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customto give the residue, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5cd70098ed70461c8d3eb91183057903
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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