Boron Trichloride → 4-Methoxy-5-methyl-2-nitrophenol

HRID 2354351노트

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HRID 2354351 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([O:8]C)[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[O:13][CH3:14].B(Cl)(Cl)Cl>C(Cl)Cl>[CH3:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([OH:8])[CH:7]=1

참가 물질

4

반응물 2

HCID 25135Boron TrichlorideHCID 27780951,4-Dimethoxy-2-methyl-5-nitrobenzene

생성물 1

HCID 574186644-Methoxy-5-methyl-2-nitrophenol수율 99.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-20 °C

실험 절차

1-Methyl-2,5-bis(methyloxy)-4-nitrobenzene (3.96 g, 20 mmol) was dissolved in CH2Cl2 (20 mL) and cooled to −20° C. A solution of BCl3 (1.0 M) in CH2Cl2 (20 mL) was added to above solution drop wise over 5 minutes. A purple solution was obtained. The reaction mixture was slowly warmed to room temperature and stirred for 20 h. The mixture was then quenched with saturated Na2CO3, stirred for 10 minutes and then extracted with EtOAc (3×100 mL). The organic extracts were combined, washed with water, brine, and dried (Na2SO4). The solvent was removed via rotovap to give the title compound (3.65 g, 99%) as a yellow solid. MS (ES) m/e 184 [M+H]+.

후처리

  1. customA purple solution was obtained
  2. temperatureThe reaction mixture was slowly warmed to room temperature
  3. customThe mixture was then quenched with saturated Na2CO3
  4. stirringstirred for 10 minutes
  5. extractionextracted with EtOAc (3×100 mL)
  6. washwashed with water, brine
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was removed via rotovap

출처 및 근거

ORD 기록
ord-797535c02a53441781def30f7c9df803
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07749998B2

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