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

HRID 2050161Notes

Reaction equation

HRID 2050161 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 (4.0g) and 1-bromo-2-(4-fluorophenyl) ethane (4.06g) in acetone (100ml) 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 (200ml) was added and the mixture filtered to remove unchanged 4-benzyloxy-7-hydroxycoumarin. Reevaporation of the filtrate afforded a white solid, 3.34g (43%) of m.p. 120°, νmax (mull) 1715, 1675, 1620cm-1 ; τ(CDCl3); 6.93 (2H, t, J 6.7 Hz); 5.80 (2H, t, J 6.7 Hz); 4.87 (4.38 (1H,); 3.29-2.49 (6H, m) 2.32 (1H, d, J 10Hz); (Found C, 73.75 H, 5.14C24H19FO4 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, 3.34g (43%) of m.p. 120°, νmax (mull) 1715, 1675, 1620cm-1

Sources & evidence

ORD record
ord-8f9b698f0e004e59940ecbefc1205ba3
Source dataset
uspto-grants-1980_04
Patent number
US04200577

Reaction notes

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