Water → HCID 19828697, compound

HRID 1494596Notes

Reaction equation

HRID 1494596 reaction equation
[Na].Br[CH2:3][C:4]1[C:5]([CH2:10]Br)=[CH:6][CH:7]=[CH:8][CH:9]=1.[C:12](#[N:17])[CH2:13][C:14]([CH3:16])=[O:15].O>C(O)C.CCOCC>[C:14]([C:13]1([C:12]#[N:17])[CH2:10][C:5]2[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH2:3]1)(=[O:15])[CH3:16]

Participants

7

Reactant 4

HCID 962WaterHCID 66665o-Bis(bromomethyl)benzeneHCID 755793-Oxobutyronitrile2×HCID 5360545Sodium

Product 1

HCID 19828697HCID 19828697, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Sodium (13.2 g) was dissolved in dry ethanol (220 ml). Dry diethyl ether (270 ml) was added. To the solution were simultaneously added α,α'-dibromo-o-xylene (85.2 g), dry ether (250 ml) and acetoacetonitrile (45.6 g) in dry ether (160 ml) over a period of one hour. (Acetoacetonitrile had been prepared by the method described in U.S. Pat. No. 4,152,336.) After the addition, the mixture was stirred for 1 hour at room temperature and then refluxed for 2 hours. The cooled reaction mixture wa poured into water. The ether layer was separated and the water layer was extracted once more with ether. The combined ether solutions were washed with water, dried (MgSO4) and evaporated. The yield of crude product was 73.8 g.

Workup

  1. customof one hour
  2. addition) After the addition
  3. temperaturerefluxed for 2 hours
  4. customThe cooled reaction mixture
  5. customThe ether layer was separated
  6. extractionthe water layer was extracted once more with ether
  7. washThe combined ether solutions were washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-ce3ba65796444f96b14e235ab63f2ab2
Source dataset
uspto-grants-1991_06
Patent number
US05026868

Reaction notes

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