Lithium Carbonate → HCID 22501823, compound

HRID 1633927Notes

Reaction equation

HRID 1633927 reaction equation
Br[C:2]1([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[Li+].[Li+].[Br-].[Li+]>CN(C=O)C.C(OCC)(=O)C>[C:2]1([C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=1

Participants

6

Reactant 3

HCID 11125Lithium CarbonateHCID 82050Lithium BromideHCID 225017731-(Bromocyclohexyl)-4-nitrobenzene

Product 1

HCID 22501823HCID 22501823, compoundYield 88.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

1-(Bromocyclohexyl)-4-nitrobenzene (18.4 g, 64.8 mmol), lithium carbonate (5.3 g, 71.2 mmol), and lithium bromide (6.2 g, 71.2 mmol) were reacted together in DMF (100 mL) for 2 hours at 160° C. The reaction mixture was cooled to 20° C., diluted with ethyl acetate (500 mL), and washed with water (300 mL). The aqueous phase was extracted with ethyl acetate (200 mL) and the combined organic phases were washed with water (3×150 mL), dried over MgSO4 and concentrated in vacuo. The residue was purified on silica (350 g) using ethyl acetate and heptane (1:9) as eluent to give 11.7 g of 1-cyclohex-1-enyl-4-nitrobenzene.

Workup

  1. washwashed with water (300 mL)
  2. extractionThe aqueous phase was extracted with ethyl acetate (200 mL)
  3. washthe combined organic phases were washed with water (3×150 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on silica (350 g)

Sources & evidence

ORD record
ord-fa6108903a1441608c79210409b84237
Source dataset
uspto-grants-2003_01
Patent number
US06503949B1

Reaction notes

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