6-Bromo-1,1,2,2-tetrafluoro-1,2-dihydronaphthalene → 5,6-Difluoro-2-bromonaphthalene

HRID 390707Notes

Reaction equation

HRID 390707 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](F)([F:12])[C:7](F)([F:14])[CH:6]=[CH:5]2>O1CCCC1.[OH-].[NH4+].ClCCl.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([F:12])=[C:7]([F:14])[CH:6]=[CH:5]2

Participants

6

Reactant 1

HCID 224834376-Bromo-1,1,2,2-tetrafluoro-1,2-dihydronaphthalene

Product 1

HCID 114138325,6-Difluoro-2-bromonaphthalene

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 14923Ammonium HydroxideSolvent

Procedure

Zinc (341 mg, 5.22 mmol) was added to a stirred mixture of 6-bromo-1,1,2,2-tetrafluoro-1,2-dihydronaphthalene (730 mg, 2.60 mmol) in tetrahydrofuran and concentrated ammonium hydroxide (4 mL) at 0° C. The mixture was allowed to warm slowly to room temperature. After 6 hours the reaction was diluted with 35 mL of dichloromethane and extracted. The organic layer was washed with water (2×30 mL) dried and concentrated. The residue was purified by chromatography on silica gel eluting with pentane:hexane (1:1) to provide the title compound.

Workup

  1. extractionextracted
  2. washThe organic layer was washed with water (2×30 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel eluting with pentane:hexane (1:1)

Sources & evidence

ORD record
ord-362adbe121754d8dbd303511c0643a06
Source dataset
uspto-grants-2013_02
Patent number
US08383657B2

Reaction notes

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