Ethyl 4-bromobenzoate → Ethyl 4-(4-n-pentyloxyphenylethynyl)benzoate

HRID 351536

반응식

HRID 351536 반응식
Br[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH2:13]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[CH:26])=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH3:17]>C(N(CC)CC)C.N1C=CC=CC=1.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:13]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[C:26][C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)=[CH:21][CH:20]=1)[CH2:14][CH2:15][CH2:16][CH3:17]

참가 물질

8

반응물 2

HCID 22043Ethyl 4-bromobenzoateHCID 27751191-Eth-1-ynyl-4-(pentyloxy)benzene

생성물 1

HCID 22713259Ethyl 4-(4-n-pentyloxyphenylethynyl)benzoate수율 35.2%

시약·촉매·용매 5

HCID 11776Triphenylphosphine촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 1049Pyridine용매HCID 8471Triethylamine용매

반응 조건

온도
80 °C

실험 절차

To a suspension of ethyl 4-bromobenzoate (1.37 g), (4-n-pentyloxyphenyl)acetylene (565 mg), triphenylphosphine (16 mg) and copper(I) iodide (6 mg) in triethylamine (10 ml) and pyridine (4 ml) was added palladium(II) chloride bis(triphenylphosphine) (21 mg) and the reaction mixture was stirred for 24 hours at 80° C. After cooling, the precipitate was filtered off, and the filtrate was evaporated under reduced pressure. The residue was taken up to dichloromethane, and the solution was washed successively with 1N HCl, water, brine and dried over magnesium sulfate. The solvents were removed under reduced pressure and the residue was triturated with acetonitrile, collected by filtration and dried under reduced pressure to give ethyl 4-(4-n-pentyloxyphenylethynyl)benzoate (355 mg).

후처리

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off
  3. customthe filtrate was evaporated under reduced pressure
  4. washthe solution was washed successively with 1N HCl, water, brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvents were removed under reduced pressure
  7. customthe residue was triturated with acetonitrile
  8. filtrationcollected by filtration
  9. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-75df36affa3b4e1c9e154e2606ab4cdf
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743776B2

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