Dimethyl Sulfoxide → HCID 86674624, compound

HRID 1851674Notes

Reaction equation

HRID 1851674 reaction equation
CS(C)=O.[NH:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13](Br)[CH:12]=1.[OH-].[K+]>C(OC(=O)C)C>[F:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([N:5]2[CH:9]=[CH:8][N:7]=[CH:6]2)[CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 795ImidazoleHCID 14797Potassium HydroxideHCID 1362922-Bromo-4-fluoroanisole

Product 1

HCID 86674624HCID 86674624, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a degassed DMSO (20 mL) solution of imidazole (1.0 g, 15 mmol) was added 4-fluoro-2-bromoanisole (1.25 mL, 10 mmol), KOH (1.12 g, 20 mmol) and Cu2O (280 mg, 2 mmol) under nitrogen. The resulting mixture was stirred at 140° C. for 24 hrs under N2. After cooling to room temperature, the mixture was poured into ethylacetate (EA) (50 mL) and filtered. The filtrate was washed with water (50 mL×3) and dried over anhydrous magnesium sulfate. After rotary evaporation, the crude oil was purified via column chromatography on silica gel with eluent of EA/MeOH (9/1, v/v), affording a light yellow liquid (47%). 1H-NMR (400 MHz, CDCl3) δ(ppm) 7.82 (s, 1H), 7.21 (m, 1H), 7.17 (m, 1H), 7.07 (m, 2H), 7.00 (m, 1H), 3.84 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with water (50 mL×3)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter rotary evaporation
  6. customthe crude oil was purified via column chromatography on silica gel with eluent of EA/MeOH (9/1

Sources & evidence

ORD record
ord-b32d0f2870014038bcb4fdbbb1607656
Source dataset
uspto-grants-2015_02
Patent number
US08957217B2

Reaction notes

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