1-Bromo-2-fluorobenzene → 5-(2-Fluorophenyl)pent-4-yn-1-ol

HRID 72103

반응식

HRID 72103 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[F:8].[CH2:9]([OH:14])[CH2:10][CH2:11][C:12]#[CH:13]>C(#N)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:13]#[C:12][CH2:11][CH2:10][CH2:9][OH:14]

참가 물질

6

반응물 2

HCID 612591-Bromo-2-fluorobenzeneHCID 793464-Pentyn-1-ol

생성물 1

HCID 866878565-(2-Fluorophenyl)pent-4-yn-1-ol

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 6342Acetonitrile용매

실험 절차

1-Bromo-2-fluorobenzene [1072-85-1] (3.0 g, 17 mmol, 1.0 equiv) and pent-4-yn-1-ol [5390-04-5] (2.3 mL, 25 mmol, 1.5 equiv) were dissolved in acetonitrile (40 mL). CuI (0.13 g, 0.68 mmol, 0.04 equiv) and TEA (3.4 mL, 25 mmol, 1.5 equiv) was added to the stirred solution followed by tetrakis(triphenylphosphine)palladium(0) (0.39 g, 0.34 mmol, 0.02 equiv). The solution was heated at reflux for 16 hours. The solution was cooled, filtered through Celite, the Celite pad rinsed with EtOAc and the solvent removed by rotoevaporation. Column chromatography (9:1 hexanes:ethyl acetate) of the residue afforded pure 5-(2-fluorophenyl)pent-4-yn-1-ol Intermediate 60 (1.3 g, 43%).

후처리

  1. temperatureThe solution was heated
  2. temperatureat reflux for 16 hours
  3. temperatureThe solution was cooled
  4. filtrationfiltered through Celite
  5. washthe Celite pad rinsed with EtOAc
  6. customthe solvent removed by rotoevaporation

출처 및 근거

ORD 기록
ord-aba1e866d2cd413daa1a31e8afd20c22
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08828973B2

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