3-Fluorophenol → 1-Fluoro-3-(prop-2-yn-1-yloxy)benzene

HRID 1912620

反応式

HRID 1912620 の反応式
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[C:16]#[C:17][CH3:18]>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:18][C:17]#[CH:16])[CH:3]=1

参加物

6

反応物 3

HCID 97433-FluorophenolHCID 11430Potassium CarbonateHCID 1372791-Propyne, 1-bromo-

生成物 1

HCID 145131821-Fluoro-3-(prop-2-yn-1-yloxy)benzene収率 106.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

3-Fluorophenol (5.10 g, 45.5 mmol) was dissolved in DMF (10 mL) and potassium carbonate (7.55 g, 54.6 mmol) was added and the mixture was stirred at ambient temperature for 30 minutes. Bromoprop-1-yne (5.05 mL, 45.5 mmol) was added and the reaction was stirred overnight at ambient temperature. The mixture was diluted with water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, concentrated under reduced pressure to give a yellow oil (7.27 g) that was used without further purification in the next step. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm=7.30-7.23 (m, 1 H), 6.81-6.69 (m, 3 H), 4.70 (d, J=2.3 Hz, 2 H), 2.56 (t, 1 H); LCMS (m/z) ES+=151 (M+1).

後処理

  1. stirringthe reaction was stirred overnight at ambient temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-dc7ebb8c68714bfe81486ce82c7fbce3
出典データセット
uspto-grants-2013_12
特許番号
US08609653B2

関連ノート

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