Chloroform → 4-Benzyloxy-7-(2-[4-fluorophenyl]ethoxy)coumarin

HRID 1706457Notes

Reaction equation

HRID 1706457 reaction equation
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([OH:19])=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1.C(Cl)(Cl)Cl>CC(C)=O>[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([O:19][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=3)=[CH:16][CH:17]=2)[O:12][C:11](=[O:20])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 11430Potassium CarbonateHCID 5731534-Fluorophenethyl bromideHCID 134084074-Benzyloxy-7-hydroxycoumarin

Product 1

HCID 227513064-Benzyloxy-7-(2-[4-fluorophenyl]ethoxy)coumarin

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-benzyloxy-7-hydroxycoumarin (5.36; 0.02 mole) anhydrous potassium carbonate (4.0 g) and 1-bromo-2-(4-fluorophenyl) ethane (4.06 g) in acetone (100 ml) was stirred at reflux for 20 hours and the inorganic material filtered off. Evaporation of the filtrate in vacuo gave an oil which rapidly set solid on scratching. Chloroform (200 ml) was added and the mixture filtered to remove unchanged 4-benzyloxy-7-hydroxycoumarin. Reevaporation of the filtrate afforded a white solid, 3.34 g (43%) of m.p. 120°, νmax (mull) 1715, 1675, 1620 cm-1 ; τ(CDCl3); 6.93 (2H, t, J 6.7 Hz); 5.80 (2H, t, J 6.7 Hz); 4.87 (2H,S); 4.38 (1H,); 3.29-2.49 (6H, m) 2.32 (1H, d, J 10 Hz); (Found C, 73.75 H, 5.14 C24H19FO4 requires; C, 73.84; H, 4.91%).

Workup

  1. temperatureat reflux for 20 hours
  2. filtrationthe inorganic material filtered off
  3. customEvaporation of the filtrate in vacuo
  4. customgave an oil which rapidly set solid
  5. filtrationthe mixture filtered
  6. customto remove unchanged 4-benzyloxy-7-hydroxycoumarin
  7. customReevaporation of the filtrate
  8. customafforded a white solid, 3.34 g (43%) of m.p. 120°, νmax (mull) 1715, 1675, 1620 cm-1

Sources & evidence

ORD record
ord-f5ecc34535f14491aea18c4614b43da0
Source dataset
uspto-grants-1980_06
Patent number
US04207335

Reaction notes

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