Propargyl bromide → Methyl 4-fluoro-3-(prop-2-yn-1-yloxy)benzoate

HRID 1531430Notes

Reaction equation

HRID 1531430 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].[CH2:13](Br)[C:14]#[CH:15].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:15][C:14]#[CH:13]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 120168924-Fluoro-3-hydroxy-benzoic acid methyl ester

Product 1

HCID 11138296Methyl 4-fluoro-3-(prop-2-yn-1-yloxy)benzoateYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl 4-fluoro-3-hydroxybenzoate (20.0 mL, 0.118 mol) was dissolved in anhydrous acetone (450 mL), mixed with propargyl bromide (26.2 g, 0.177 mol) followed by the addition of powdered K2CO3 (32.4 g, 0.236 mol) and the reaction mixture was stirred overnight at room temperature. The reaction was filtered and the solvent was removed in vacuo. The residue was dissolved in diethyl ether, washed 4 times with H2O, treated with brine, dried with MgSO4, filtered, and the solvent was removed in vacuo to give 25.5 g (100% yield) of a light peach coloured solid as the title compound (mp 60.5-61.5° C.). Mass spectrum (70 eV) m/z (relative intensity) 208 (27, M+), 207 (100), 193 (22), 177 (20), 149 (50), 82 (21), 81 (10).

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washwashed 4 times with H2O
  5. additiontreated with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. customthe solvent was removed in vacuo
  9. customto give 25.5 g (100% yield) of a light peach

Sources & evidence

ORD record
ord-5f108b1ccaf74bc7bda49d3be62d84cf
Source dataset
uspto-grants-2001_03
Patent number
US06197978B1

Reaction notes

Loading…