Water → HCID 16756659, compound

HRID 453099Notes

Reaction equation

HRID 453099 reaction equation
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:14]=[C:13]([CH2:15]O)[S:12][N:11]=2)=[CH:6][CH:5]=1.P(Br)(Br)[Br:20].O>C1(C)C=CC=CC=1>[Br:20][CH2:15][C:13]1[S:12][N:11]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:18])([F:17])[F:1])=[CH:5][CH:6]=2)[N:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 16756658HCID 16756658, compound

Product 1

HCID 16756659HCID 16756659, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of [3-(4-trifluoromethoxyphenyl)-[1,2,4]thiadiazol-5-yl]-methanol (0.10 g, 0.36 mmol) in toluene (5 ml) was added PBr3 (0.050 ml, 0.54 mmol) and the resulting reaction mixture was refluxed at 120° C. for 15 min. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to 0° C., added water (50 ml) and extracted with ethyl acetate (3×50 ml). The combined organics was washed with saturated NaHCO3 solution, dried over Na2SO4, filtered and concentrated under vacuum to get the desired product (0.11 g, 89%).

Workup

  1. customthe resulting reaction mixture
  2. customAfter the completion of the reaction (TLC monitoring)
  3. temperaturethe reaction mixture was cooled to 0° C.
  4. extractionextracted with ethyl acetate (3×50 ml)
  5. washThe combined organics was washed with saturated NaHCO3 solution
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9df481b9df4c4e2c932421dce3d79405
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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