Iodobenzene → 5-phenoxy-3,4-dihydronaphthalen-1(2H)-one

HRID 1847187Notes

Reaction equation

HRID 1847187 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12].I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Na+].COCCOCCN(CCOCCOC)CCOCCOC>CN(C=O)C.O.Cl[Cu]>[O:1]([C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][C:7]2=[O:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 11575IodobenzeneHCID 24758Sodium hydrideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 1199215-Hydroxy-1-tetralone

Product 1

HCID 107286255-phenoxy-3,4-dihydronaphthalen-1(2H)-oneYield 18%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-hydroxy-1-tetralone (4.5 g, 28.0 mmol) and iodobenzene (24.0 g, 168.0 mmol) in DMF (50 mL) was added NaH (1.2 g, 30.0 mmol) at room temperature. The mixture was heated to 50° C. until the solid was dissolved and then cooled. To the mixture was added CuCl (2.8 g, 28.0 mmol); followed by tris(dioxa 3,6-heptyl)amine (2.7 g, 8.4 mmol). The mixture was heated at 145° C. overnight. The reaction was diluted with water, extracted with EtOAc, washed with brine, dried (Na2SO4), and concentrated. Purification by silica gel chromatography (20:1 PE/EtOAc) gave 1.2 g (18%) of the title compound as a yellow oil. [M+H] calc'd for C16H14O2, 239. Found 239.

Workup

  1. dissolutionwas dissolved
  2. temperaturecooled
  3. temperatureThe mixture was heated at 145° C. overnight
  4. extractionextracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customPurification by silica gel chromatography (20:1 PE/EtOAc)

Sources & evidence

ORD record
ord-8ff5dc5186c049c1b25b6d8c8c39a8a2
Source dataset
uspto-grants-2015_02
Patent number
US08952151B2

Reaction notes

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