Potassium Carbonate → HCID 86683817, compound

HRID 1620325Notes

Reaction equation

HRID 1620325 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH2:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1F)[CH:21]=[O:22].[OH-].[Na+]>CS(C)=O>[Br:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([CH2:9][CH3:10])[CH:4]=1)[CH:21]=[O:22]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 842234-Chloro-3-ethylphenolHCID 1736043-Bromo-4-fluorobenzaldehyde

Product 1

HCID 86683817HCID 86683817, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of DMSO (10 mL) was added 4-chloro-3-ethylphenol (5 g, 31.9 mmol), followed by potassium carbonate (11.0 g, 79.8 mmol). After 1 minute, 3-bromo-4-fluorobenzaldehyde (6.48 g, 31.9 mmol) was added in one portion, and the reaction heated to 50° C. for 5 hours. The reaction was diluted by addition of 1M NaOH solution (100 mL), and extracted into ethyl acetate (3×100 mL). The combined organic layers were then dried over magnesium sulfate, filtered, and concentrated in vacuo to leave a crude pink oil. The crude material was purified by column chromatography (silica), eluting with 4:1 heptane:ethyl acetate, the title compound as a white solid (8.22 g, 76%).

Workup

  1. extractionextracted into ethyl acetate (3×100 mL)
  2. dry with materialThe combined organic layers were then dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto leave a crude pink oil
  6. customThe crude material was purified by column chromatography (silica)
  7. washeluting with 4:1 heptane

Sources & evidence

ORD record
ord-08e96799fa7d42488fffc20b0955f60f
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

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