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

HRID 1912620Notes

Reaction equation

HRID 1912620 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-dc7ebb8c68714bfe81486ce82c7fbce3
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

Loading…