Water → 2-fluoro-5H-dibenzo[a,d]cycloheptene

HRID 47221Notes

Reaction equation

HRID 47221 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[F:11][C:12]1[CH:27]=[CH:26][C:15]2[C:16](=O)[C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH:19]=[CH:20][C:14]=2[CH:13]=1.O>O1CCCC1.C(Cl)Cl>[F:11][C:12]1[CH:27]=[CH:26][C:15]2[CH2:16][C:17]3[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=3[CH:19]=[CH:20][C:14]=2[CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 14204212HCID 14204212, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 227441622-fluoro-5H-dibenzo[a,d]cyclohepteneYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

LiAlH4 (0.0686 mol) was added dropwise to a suspension of AlCl3 (0.0718 mol) in tetrahydrofuran (75 ml), cooled on an ice-bath and under N2 atmosphere. The mixture was stirred for 10 minutes at 0° C. A solution of 2-fluoro-5H-dibenzo[a,d]cyclohepten-5-one (0.0653 mol and prepared as described in DE 3,644,462) in tetrahydrofuran (75 ml) was added dropwise and the resulting reaction mixture was allowed to warm to room temperature. Then, the reaction mixture was stirred and refluxed for 2 hours. The mixture was cooled on an ice-bath. Water and CH2Cl2 was added. The organic layer was washed with a saturated aqueous NaHCO3 solution, dried, filtered and the solvent was evaporated, yielding 13.16 g (96%) of 2-fluoro-5H-dibenzo[a,d]cycloheptene (intermediate 1)

Workup

  1. temperaturecooled on an ice-bath and under N2 atmosphere
  2. customthe resulting reaction mixture
  3. temperatureto warm to room temperature
  4. stirringThen, the reaction mixture was stirred
  5. temperaturerefluxed for 2 hours
  6. temperatureThe mixture was cooled on an ice-bath
  7. washThe organic layer was washed with a saturated aqueous NaHCO3 solution
  8. customdried
  9. filtrationfiltered
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-2d7d19c670754520a27155e45e31aceb
Source dataset
uspto-grants-2004_03
Patent number
US06699858B2

Reaction notes

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