Triethylamine → HCID 734136, compound

HRID 1866113Notes

Reaction equation

HRID 1866113 reaction equation
[Cl].[Br:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](O)=[CH:15][CH:14]=1.C(N(CC)CC)C>O1CCOCC1>[F:12][C:13]1[CH:18]=[CH:17][C:16]([O:8][C:7](=[O:9])[C:6]2[CH:10]=[CH:11][C:3]([Br:2])=[CH:4][CH:5]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 97324-FluorophenolHCID 178524194HCID 178524194, compound

Product 1

HCID 734136HCID 734136, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Ten ml of dioxane, 5 mmol (1.1 g) of 4-bromo-benzoic acid chlorine, and 5 mmol (0.56 g) of 4-fluoro-phenol were added to 50 ml four-mouth-flask sequentially and dissolved at room temperature. Triethylamine dissolved in dioxane was slowly dripped into this solution and the solution was stirred for three hours at room temperature. The precipitated crystals were filtered and extracted with benzene. The extracted solution was washed with sodium hydrocarbonate several times, magnesium anhydrate was added, and the resulting solution was dried and filtered. The solution was distilled under low pressure and crystallized. The row crystals were yellowish-white, weighing 1.37 g. A portion of this crystal (0.5 g) was dissolved in benzene and purified with 100 g of silica gel (Wako gel C-300, Japan). The purified product was white, and the purity was confirmed to 99.93% by liquid chromatography (LC). The structure was confirmed by NMR as follows. 1H NMR (400 MHz, DMSO-d6) δ 8.05 (2H, d, J=8.8 Hz), 7.83 (2H, d, J=8.8 Hz), 7.38˜7.29 (4H, m) 13C NMR (100 MHz, DMSO-d6) δ 159.72 (C—F, d, J=240 Hz) 163.95 (C═O)

Workup

  1. dissolutiondissolved at room temperature
  2. filtrationThe precipitated crystals were filtered
  3. extractionextracted with benzene
  4. washThe extracted solution was washed with sodium hydrocarbonate several times, magnesium anhydrate
  5. additionwas added
  6. customthe resulting solution was dried
  7. filtrationfiltered
  8. distillationThe solution was distilled under low pressure
  9. customcrystallized
  10. dissolutionA portion of this crystal (0.5 g) was dissolved in benzene
  11. custompurified with 100 g of silica gel (Wako gel C-300, Japan)

Sources & evidence

ORD record
ord-165af90109f146349388837c45b7da10
Source dataset
uspto-grants-2009_12
Patent number
US07629364B2

Reaction notes

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