Water → Naphthalene, 1,2-dihydro-3-(4-methoxy-2-nitrophenyl)-7-(phenylmethoxy)-

HRID 1950110Notes

Reaction equation

HRID 1950110 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14](Br)[CH2:15][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=1[N+:29]([O-:31])=[O:30].C(OCC)(=O)C.O>CS(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][C:22]=3[N+:29]([O-:31])=[O:30])[CH2:15][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 792884-Bromo-3-nitroanisoleHCID 230874203-Bromo-1,2-dihydro-7-(phenylmethoxy)naphthalene

Product 1

HCID 23087493Naphthalene, 1,2-dihydro-3-(4-methoxy-2-nitrophenyl)-7-(phenylmethoxy)-Yield 40.7%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

The title compound was synthesized by referring to Tetrahedron Lett., 1993, 34 (21), 3421. A suspension of 7-benzyloxy-3-bromo-1,2-dihydronaphthalene (38 g), 4-bromo-3-nitroanisole (59 g), dichlorobis(triphenylphosphine)palladium (II) (4.5 g) and copper (32 g) in dimethyl sulfoxide (400 ml) was stirred under a nitrogen atmosphere at 120° C. for 1 hour. Ethyl acetate and water was added thereto, the solution was filtered through celite pad, extracted with ethyl acetate, then sequentially washed with aqueous ammonia, water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (19 g).

Workup

  1. customThe title compound was synthesized
  2. filtrationthe solution was filtered through celite pad
  3. extractionextracted with ethyl acetate
  4. washsequentially washed with aqueous ammonia, water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-f87c9c81475c49b79e5e359fde24d31f
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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