3-Ethoxy-1-propanol → 4-Bromo-3-chloro-(3-ethoxypropoxy)benzene

HRID 1978749

반응식

HRID 1978749 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[Cl:9].[CH2:10]([O:12][CH2:13][CH2:14][CH2:15]O)[CH3:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:15][CH2:14][CH2:13][O:12][CH2:10][CH3:11])=[CH:4][C:3]=1[Cl:9]

참가 물질

5

반응물 3

HCID 81093-Ethoxy-1-propanolHCID 11776TriphenylphosphineHCID 70181824-Bromo-3-chlorophenol

생성물 1

HCID 219957444-Bromo-3-chloro-(3-ethoxypropoxy)benzene수율 79.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-bromo-3-chlorophenol (10.0 g), 3-ethoxypropanol (6.0 g) and triphenylphosphine (15.2 g) in tetrahydrofuran (50 ml) was added dropwise under nitrogen atmosphere at 0° C. diethylazodicarbonate (40% toluene solution, 25.2 g) for 15 minutes, and the mixture was stirred at room temperature for 2 hours and concentrated under reduced pressure. To the residue was added diethylether, and insoluble materials were filtered off. The filtrate was washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column chromatography (ethyl acetate/hexane 1:5) and distilled under reduced pressure (1.5 mmHg, 190° C.) to give colorless oil of 4-bromo-3-chloro-(3-ethoxypropoxy)benzene (11.2 g).

후처리

  1. concentrationconcentrated under reduced pressure
  2. additionTo the residue was added diethylether, and insoluble materials
  3. filtrationwere filtered off
  4. washThe filtrate was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customthe residue was purified with silica gel column chromatography (ethyl acetate/hexane 1:5)
  8. distillationdistilled under reduced pressure (1.5 mmHg, 190° C.)

출처 및 근거

ORD 기록
ord-27b5571bb6ef4756afb09de3f411e840
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06235771B1

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