7-Bromo-1,2,3,4-tetrahydronaphthalen-1-one → HCID 18960968, compound

HRID 1708129Notes

Reaction equation

HRID 1708129 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[F:13][C:14]([F:22])([F:21])[C:15]([F:20])([F:19])C([O-])=O.[Na+]>CN1CCCC1=O.[Cu]I>[F:19][C:15]([F:20])([C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:12])=[CH:4][CH:3]=1)[C:14]([F:22])([F:21])[F:13]

Participants

5

Reactant 2

HCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-oneHCID 2733305Sodium pentafluoropropionate

Product 1

HCID 18960968HCID 18960968, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 10 g (0.044 mol) of 7-bromo-1,2,3,4-tetrahydronaphthalenone in 300 mL of N-methylpyrrolidone was added 32.23 g (0.17 mol) of CuI and 31.59 g (0.17 mol) of sodium pentafluoropropanoate and the mixture was heated for 3 h at reflux under an argon atmosphere. After cooling to room temperature, the resulting suspension was poured into a mixture of H2O--Et2O (1:1) and filtered over celite. The layers were separated and the organic phase was washed with H2O and dried over MgSO4. The solvent was removed, to afford a residue that was chromatographed on silica gel (hexane-AcOEt), to give the desired product as a colourless oil (8.75 g, yield: 80%).

Workup

  1. temperaturethe mixture was heated for 3 h
  2. temperatureat reflux under an argon atmosphere
  3. additionthe resulting suspension was poured into a mixture of H2O--Et2O (1:1)
  4. filtrationfiltered over celite
  5. customThe layers were separated
  6. washthe organic phase was washed with H2O
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed
  9. customto afford a residue that
  10. customwas chromatographed on silica gel (hexane-AcOEt)

Sources & evidence

ORD record
ord-aa0504312d864e5b9b58d58be25e9cb3
Source dataset
uspto-grants-1994_10
Patent number
US05356915

Reaction notes

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