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

HRID 453114Notes

Reaction equation

HRID 453114 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH2:13]O)[S:10][N:9]=2)=[C:4]([O:15][CH3:16])[CH:3]=1.P(Br)(Br)[Br:18].O>C1(C)C=CC=CC=1>[Br:18][CH2:13][C:11]1[S:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[O:15][CH3:16])[N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 59549528(3-(4-Chloro-2-methoxyphenyl)-1,2,4-thiadiazol-5-yl)methanol

Product 1

HCID 595495315-(Bromomethyl)-3-(4-chloro-2-methoxyphenyl)-1,2,4-thiadiazoleYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (3-(4-chloro-2-methoxyphenyl)-1,2,4-thiadiazol-5-yl)methanol (0.08 g, 0.31 mmol) in toluene (4 ml) was added PBr3 (49 μl, 0.47 mmol) and the resulting reaction mixture was heated at 60° C. for 2 h. 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. The crude residue was purified over silica gel (100-200 M, 5% EtOAc-Hexane) to get the desired product (0.063 g, 64%). MS: 319 (M+H)+.

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
  9. customThe crude residue was purified over silica gel (100-200 M, 5% EtOAc-Hexane)

Sources & evidence

ORD record
ord-8ad3327282d046898f49098c9cd5add3
Source dataset
uspto-grants-2013_07
Patent number
US08492414B2

Reaction notes

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