Ethyl Acetate → HCID 21907868, compound

HRID 984934Notes

Reaction equation

HRID 984934 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:18]=[CH:17][C:7]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)=O)=[CH:6][CH:5]=1.[C:19]([O:22][CH2:23][CH3:24])(=[O:21])[CH3:20]>C1COCC1.Cl>[CH2:23]([O:22][C:19](=[O:21])[CH:20]=[C:8]([C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)[C:7]1[CH:17]=[CH:18][C:4]([Br:3])=[CH:5][CH:6]=1)[CH3:24]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 728684,4'-Dibromobenzophenone

Product 1

HCID 21907868HCID 21907868, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of triethyl phosphonoacetate (26.8 g, 120.0 mmol) in dry THF (100 mL) was added at 0° C. over a period of 25 min. to a stirred suspension of sodium hydride (60% in oil, 4.8 g, 120.0 mmol) in dry THF (100 ml). After stirring at 0° C. for 30 min. a solution of 4,4′-dibromobenzophenone (20.4 g, 60.0 mmol) in dry THF (200 ml) was added and the mixture slowly warmed to room temperature, and stirring continued for 48 h. The reaction mixture was diluted with 1N hydrochloric acid (400 ml) and ethyl acetate (100 ml). The organic phase was separated, and the aqueous phase further extracted with ethyl acetate (2×300 ml). The combined organic phases were washed with water (300 ml×3), dried (MgSO4), filtered and concentrated in vacuo. The product was purified by column chromatography on silica gel (15% ethyl acetate in n-heptane eluent) to give 24.5 g (99%) 3,3-bis-(4-bromophenyl)-acrylic acid ethyl ester as an off-white amorphous solid.

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. extractionthe aqueous phase further extracted with ethyl acetate (2×300 ml)
  4. washThe combined organic phases were washed with water (300 ml×3)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by column chromatography on silica gel (15% ethyl acetate in n-heptane eluent)

Sources & evidence

ORD record
ord-9d27f9bb31a14003a8d16fa5f67e36ef
Source dataset
uspto-grants-2005_03
Patent number
US06869967B2

Reaction notes

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