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

HRID 453114노트

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HRID 453114 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
60 °C

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-8ad3327282d046898f49098c9cd5add3
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492414B2

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