4-Fluorophenol → HCID 53975395, compound

HRID 1460278Notes

Reaction equation

HRID 1460278 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[H][H].Cl[CH2:14][CH2:15][CH2:16][C:17]#[CH:18]>CS(C)=O.O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:18][CH2:17][CH2:16][C:15]#[CH:14])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 843081-Pentyne, 5-chloro-HCID 178418361HCID 178418361, compound

Product 1

HCID 53975395HCID 53975395, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 960 mg (40 mmol) of sodium hydride in 50 mL of dimethyl sulfoxide is added 4.48 g (40 mmol) of 4-fluorophenol. The mixture is stirred until hydrogen evolution has ceased and then 4.10 g (40 mmol, 4.24 mL) of 5-chloro-1-pentyne is added. The mixture is heated to 65° C. for 1 hour, is diluted with water and is extracted with hexane. The hexane extract is washed with 2.5M aqueous sodium hydroxide and saturated brine and is dried over magnesium sulfate. The dried solution is filtered and rotoevaporated to give 7.1 g (99%) of title compound. IR: (film) 3310, 1508 cm-1 ; 1H NMR (CDCl3): δ1.97 (1H, t, J=3 Hz), 1.99 (2H, p, J=6 Hz), 2.40 (2H, dt, J=3, 7 Hz), 4.03 (2H, t, J=6 Hz), 6.84 (2H, m) and 6.96 (2H, t, J=8 Hz).

Workup

  1. extractionis extracted with hexane
  2. extractionThe hexane extract
  3. washis washed with 2.5M aqueous sodium hydroxide and saturated brine
  4. dry with materialis dried over magnesium sulfate
  5. filtrationThe dried solution is filtered

Sources & evidence

ORD record
ord-b14bcf87854c48ecb69d563f72e6e884
Source dataset
uspto-grants-1991_12
Patent number
US05070207

Reaction notes

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