Hydrochloric Acid → 1-(4-bromophenyl)-3-(furan-2-yl)prop-2-en-1-one

HRID 709174Notes

Reaction equation

HRID 709174 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[CH:16]=O.CO[Na].Cl>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH:9]=[CH:16][C:12]2[O:11][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7362FurfuralHCID 7466p-BromoacetophenoneHCID 178418582HCID 178418582, compound

Product 1

HCID 31238431-(4-bromophenyl)-3-(furan-2-yl)prop-2-en-1-oneYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromophenylethanone (112.6 g, 570 mmol) and furan-2-carbaldehyde (58.5 g, 610 mmol) in methanol (1.5 L) was added CH3ONa (31 g, 570 mmol) over 10 min and the reaction solution was stirred at room temperature overnight. The reaction mixture was neutralized with conc. HCl to pH=7, and the solvent was removed under reduced pressure. To the resultant residue was added EA and water. The aqueous layer was extracted with EA for 3 times. The combined layers were washed with brine, dried over MgSO4, concentrated and purified by silica gel column chromatography (PE (petroleum ether): EA (ethyl acetate)=10:1) to afford 1-(4-bromophenyl)-3-(furan-2-yl)prop-2-en-1-one (5A) as a yellow solid (90.2 g, 65%).

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionTo the resultant residue was added EA and water
  3. extractionThe aqueous layer was extracted with EA for 3 times
  4. washThe combined layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (PE (petroleum ether): EA (ethyl acetate)=10:1)

Sources & evidence

ORD record
ord-224f7cdd5a654bb4ab5e0922861c415e
Source dataset
uspto-grants-2015_11
Patent number
US09180119B2

Reaction notes

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