Hydrochloric Acid → HCID 468134, compound

HRID 77666Notes

Reaction equation

HRID 77666 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13](=[O:26])[CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[C:18]([O:24]C)[CH:17]=2)[CH:6]=[CH:7][C:8]=1[O:9]C.B(Br)(Br)Br.Cl>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13](=[O:26])[CH:14]=[CH:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:24])[CH:17]=2)[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 4639041,5-Bis(3,4-dimethoxyphenyl)-1,4-pentadien-3-one

Product 1

HCID 468134HCID 468134, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

1,5-Bis(3,4-dimethoxyphenyl)-1,4-pentadien-3-one (20i, 0.56 g, 1.6 mmol) was dissolved in dichloromethane (10 ml) and stirred under a nitrogen atmosphere at −78° C. for 5 min. Boron tribromide (0.90 ml, 9.5 mmol) was added and stirring continued for 60 min at −78° C., 60 min at 0° C. and 60 min at room temperature. The mixture was poured into hydrochloric acid (30 ml, 1 N) and stirring was continued for 18 hr at room temperature. The resulting mixture was extracted into ethyl acetate, washed with water and saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to afford a solid. The crude solid was chromatographed on silica gel with ethyl acetate/hexane to give 0.36 g (76%) of an orange solid: mp>250° C. [expected mp 221-223° C.]; 1H NMR: (DMSO) δ 6.78 (d, 2H, J=8.1 Hz), 6.99 (d, 2H, J=15.9 Hz), 7.06 (d, 2H, J=7.9 Hz), 7.14 (s, 2H), 7.55 (d, 2H, J=15.7 Hz), 9.15 (s, 2H), 9.63 (s, 2H); 13C NMR: (DMSO) δ 114.9, 115.6, 121.5, 122.5, 126.2, 142.5, 145.4, 148.2, 187.6.

Workup

  1. stirringstirring
  2. waitcontinued for 60 min at −78° C., 60 min at 0° C. and 60 min at room temperature
  3. stirringstirring
  4. waitwas continued for 18 hr at room temperature
  5. extractionThe resulting mixture was extracted into ethyl acetate
  6. washwashed with water and saturated sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customto afford a solid
  11. customThe crude solid was chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-1cc91c469d244dbb9c431b204c5f263f
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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