Phosphorus tribromide → 2-(Bromomethyl)-1-chloro-3-methoxybenzene

HRID 1946316ノート

反応式

HRID 1946316 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[CH2:10]O.P(Br)(Br)[Br:13].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:9][O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[CH2:10][Br:13]

参加物

5

反応物 3

HCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 28945846(2-Chloro-6-methoxyphenyl)methanol

生成物 1

HCID 223274432-(Bromomethyl)-1-chloro-3-methoxybenzene

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-10 °C

実験手順

[2-Chloro-6-(methyloxy)phenyl]methanol (0.224 g, 1.30 mmol) in dry dichloromethane (4.5 ml) under nitrogen was stirred and cooled to −10° C. A solution of phosphorus tribromide (0.357 g, 1.32 mmol, Aldrich) in dry dichloromethane (4.5 ml) was added dropwise over about 40 min. The reaction temperature was slowly allowed to warm to 5° C. over about six hours then cooled to 0° C. and saturated aqueous sodium bicarbonate (5 ml) was added. The layers were separated and the aqueous phase further extracted with chloroform. The combined organic extract was dried with magnesium sulphate, filtered and solvent evaporated in vacuo to give the title compound as a slightly yellow solid (0.232 g); LCMS: (System 4) tRET=3.07 min (no MH+ detected).

後処理

  1. temperatureto warm to 5° C. over about six hours
  2. temperaturethen cooled to 0° C.
  3. customThe layers were separated
  4. extractionthe aqueous phase further extracted with chloroform
  5. extractionThe combined organic extract
  6. dry with materialwas dried with magnesium sulphate
  7. filtrationfiltered
  8. customsolvent evaporated in vacuo

出典と根拠

ORDレコード
ord-7568c16489224aa2986e36484dfa902c
出典データセット
uspto-grants-2013_03
特許番号
US08399436B2

反応ノート

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