Sodium hydride → HCID 58197381, compound

HRID 472983Notes

Reaction equation

HRID 472983 reaction equation
Br[CH2:2][CH2:3][C:4]1[C:9]([F:10])=[C:8]([F:11])[CH:7]=[CH:6][C:5]=1[CH2:12]Br.[Br:14][C:15]1[CH:23]=[C:22]2[C:18]([CH2:19][CH2:20][C:21]2=[O:24])=[CH:17][CH:16]=1.[H-].[Na+]>C1COCC1>[Br:14][C:15]1[CH:23]=[C:22]2[C:18]([CH2:19][C:20]3([C:21]2=[O:24])[CH2:2][CH2:3][C:4]2[C:5](=[CH:6][CH:7]=[C:8]([F:11])[C:9]=2[F:10])[CH2:12]3)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1397781-Indanone, 6-bromo-HCID 58197660HCID 58197660, compound

Product 1

HCID 58197381HCID 58197381, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(2-bromoethyl)-1-(bromomethyl)-3,4-difluorobenzene (3 g, 9.62 mmol) and 6-bromo-2,3-dihydro-1H-inden-1-one (2.03 mg, 9.62 mmol) in THF (20 mL) was added NaH (0.58 mg, 14.43 mmol), and the mixture was refluxed for 2 hour. The reaction was cooled and quenched with ice-water. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to give the residue, which was purified by preparative TLC to afford 6-bromo-5′,6′-difluoro-3′,4′-dihydro-1′H-spiro[indene-2,2′-naphthalen]-1(3H)-one (1.6 g, 46%). 1H NMR (CDCl3): 1.68 (m, 1H), 2.01 (m, 1H), 2.47 (d, 1H), 2.72 (m, 2H), 2.89 (d, 1H), 3.07 (m, 2H), 6.71 (m, 1H), 6.86 (m, 1H), 7.22 (d, 1H), 7.63 (d, 1H), 7.92 (s, 1H).

Workup

  1. temperaturethe mixture was refluxed for 2 hour
  2. temperatureThe reaction was cooled
  3. customquenched with ice-water
  4. extractionThe mixture was extracted with EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the residue, which
  10. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-e7319b5bd7f84b8580fbc73426453f60
Source dataset
uspto-grants-2014_01
Patent number
US08633212B2

Reaction notes

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