2-Bromobenzaldehyde → 2-((4-Methoxyphenyl)ethynyl)benzaldehyde

HRID 1958215노트

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HRID 1958215 반응식
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][CH:13]=1>C(N(CC)CC)C.[Cu]I>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:14][CH:13]=1

참가 물질

5

반응물 2

HCID 811292-BromobenzaldehydeHCID 2510201-Ethynyl-4-methoxybenzene

생성물 1

HCID 129972402-((4-Methoxyphenyl)ethynyl)benzaldehyde수율 89%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8471Triethylamine용매

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온도
50 °C

실험 절차

To a solution of 2-bromobenzaldehyde (1.85 g, 10 mmol) and 4-methoxyphenyl acetylene (1.58 g, 12 mmol) in 40 mL of triethylamine were added dichlorobis(triphenylphosphine) palladium(II) (140 mg, 2 mol %) and copper(I) iodide (20 mg, 1 mol %). The reaction mixture was heated at 50° C. under nitrogen for 3 hours. The reaction mixture was cooled to room temperature and the ammonium salt was removed by filtration. The filtrate was concentrated under reduced pressure. Purification of the crude compound by column chromatography (SilicaGel 230-400 mesh; 10% ethyl acetate in hexanes as eluent) afforded of 2-(4-methoxy phenylethynyl)benzaldehyde (2.1 g, 89%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe ammonium salt was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customPurification of the crude compound by column chromatography (SilicaGel 230-400 mesh; 10% ethyl acetate in hexanes as eluent)

출처 및 근거

ORD 기록
ord-429190a1bb41425192c702ab392ee25f
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08410109B2

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