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

HRID 1433924Notes

Reaction equation

HRID 1433924 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-fda9d973ee9f4a98b5d11358fc070fac
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

Loading…