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

HRID 1946316노트

반응식

HRID 1946316 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
-10 °C

실험 절차

[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).

후처리

  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

출처 및 근거

ORD 기록
ord-7568c16489224aa2986e36484dfa902c
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399436B2

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