Triethylamine → {2-Fluoro-3-[(trimethylsilyl)ethynyl]phenyl}methanol

HRID 1021260

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HRID 1021260 반응식
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].C(N(CC)CC)C.Br[C:15]1[C:16]([F:23])=[C:17]([CH2:21][OH:22])[CH:18]=[CH:19][CH:20]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I.CCOC(C)=O>[F:23][C:16]1[C:15]([C:2]#[C:1][Si:3]([CH3:6])([CH3:5])[CH3:4])=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:21][OH:22]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 269856463-Bromo-2-fluorobenzyl Alcohol

생성물 1

HCID 86686224{2-Fluoro-3-[(trimethylsilyl)ethynyl]phenyl}methanol

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

Under argon atmosphere, ethynyl(trimethyl)silane (9.0 ml) was mixed with triethylamine (50 ml), and (3-bromo-2-fluorophenyl)methanol, bis(triphenylphosphine)palladium chloride (II) (1.54 g), and copper iodide (420 mg) were added thereto, followed by stirring at 90° C. overnight. The reaction mixture was cooled to room temperature, and EtOAc was added thereto, followed by filtering using Celite as a filtration adjuvant. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain {2-fluoro-3-[(trimethylsilyl)ethynyl]phenyl}methanol (4.88 g).

후처리

  1. additionwere added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationby filtering
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-df3195c3b90844b58834d087b34f5f85
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716470B2

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