Sodium Carbonate → 4-Cyclohex-1-enyl-1-methoxy-2-nitro-benzene

HRID 1582140Notes

Reaction equation

HRID 1582140 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1)CCC.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]1([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1185334-Bromo-2-nitroanisoleHCID 11783615Stannane, tributyl-1-cyclohexen-1-yl-

Product 1

HCID 227195284-Cyclohex-1-enyl-1-methoxy-2-nitro-benzeneYield 74%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 2.1 g (0.0091 Mol) 4-bromo-2-nitroanisole in 50 ml dioxane were added 1.05 g (0.00091 Mol) tetrakis(triphenylphosphine)palladium, 4.03 g (0.011 Mol) tri-n-butyl-(1-cyclohex-1-enyl)-stannane and 18.3 ml 2 M aqueous Na2CO3 solution. The mixture was heated for 16 h at reflux and then poured onto water. After extraction with dichloro methane, drying of the combined organic phases over sodium sulfate and evaporation of the solvent the crude material was subjected to column chromatography (ethyl acetate/hexane 1:10) to yield 1.57 g of 4-cyclohex-1-enyl-1-methoxy-2-nitro-benzene as a yellow liquid. EI-MS m/e (%): 233 ([M]+, 100).

Workup

  1. temperatureThe mixture was heated for 16 h
  2. temperatureat reflux
  3. additionpoured onto water
  4. extractionAfter extraction with dichloro methane
  5. dry with materialdrying of the combined organic phases over sodium sulfate and evaporation of the solvent the crude material

Sources & evidence

ORD record
ord-a598bf9aaa1c4096a7b9a126cf255330
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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