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

HRID 72103

反応式

HRID 72103 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-aba1e866d2cd413daa1a31e8afd20c22
出典データセット
uspto-grants-2014_09
特許番号
US08828973B2

関連ノート

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