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

HRID 1503403Notes

Reaction equation

HRID 1503403 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][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[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][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[CH2:14][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 36118701,2-Bis(2-bromoethyl)benzene

Product 1

HCID 581973496'-bromo-5,6,8,9-tetrahydrospiro[benzo[7]annulene-7,2'-inden]-1'(3'H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-bromo-indan-1-one (300 mg, 1.43 mmol), 1,2-bis(2-bromoethyl)-benzene (414.3 mg, 1.43 mmol) in THF (10 mL) was added NaH (114 mg, 2.86 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-5,6,8,9-tetrahydrospiro[benzo[7]annulene-7,2′-inden]-1′(3′H)-one (20 mg, 5%).

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-5,6,8,9-tetrahydrospiro[benzo[7]annulene-7,2′-inden]-1′(3′H)-one (20 mg, 5%)

Sources & evidence

ORD record
ord-65235edf232f484b9114fa168133fb9f
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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