Sodium Carbonate → HCID 68815907, compound

HRID 735039Notes

Reaction equation

HRID 735039 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25](OB(O)O)=[CH:24][CH:23]=1>O1CCOCC1.CO>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 688115Ethyl trans-4-BromocinnamateHCID 17810664p-Chlorophenylboric acid

Product 1

HCID 68815907HCID 68815907, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

173 mg (0.15 mmol) of tetrakistriphenylphosphine palladium and 4.4 mL (8.8 mmol) of a 2M sodium carbonate solution is added at ambient temperature to a solution of 1.124 g (4.04 mmol) of ethyl (E)-3-(4-bromophenyl)acrylate in 50 mL of dioxane. 0.689 g (4.404 mmol) of 4-chlorophenylboric acid dissolved in 10 mL of methanol is added to this reaction mixture and refluxed for 5 hours. The reaction mixture is evaporated down, the residue is taken up in dichloromethane, and extracted with water. The organic phase is dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (eluant: petroleum ether/ethyl acetate (9:1)). Yield: 0.94 g (74.4% of theory); C17H15ClO2 (M=286.76); calc.: molecular ion peak (M+H)+: 287/289; found: molecular ion peak (M+H)+: 287/289; Rf value: 0.44 (silica gel, petroleum ether/ethyl acetate (40:10)).

Workup

  1. additionis added to this reaction mixture
  2. temperaturerefluxed for 5 hours
  3. customThe reaction mixture is evaporated down
  4. extractionextracted with water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customThe purification

Sources & evidence

ORD record
ord-703776c8abdd43cfa88005a55fef66f0
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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