Water → 5-Bromomethyl-3-(4-methoxyphenyl)-[1,2,4]thiadiazole

HRID 453098Notes

Reaction equation

HRID 453098 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]=[C:12]([CH2:14]O)[S:11][N:10]=2)=[CH:5][CH:4]=1.P(Br)(Br)[Br:17].O>C1(C)C=CC=CC=1>[Br:17][CH2:14][C:12]1[S:11][N:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 25132885[3-(4-Methoxyphenyl)-[1,2,4]thiadiazol-5-yl]-methanol

Product 1

HCID 595495215-Bromomethyl-3-(4-methoxyphenyl)-[1,2,4]thiadiazoleYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of [3-(4-methoxyphenyl)-[1,2,4]thiadiazol-5-yl]-methanol (0.07 g, 0.29 mmol) in toluene (10 ml) was added PBr3 (0.041 ml, 0.43 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 (0.048 g, 53%).

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-d792bdd49d2e420aa76934d16481e296
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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