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

HRID 453114ノート

反応式

HRID 453114 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-8ad3327282d046898f49098c9cd5add3
出典データセット
uspto-grants-2013_07
特許番号
US08492414B2

反応ノート

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