Ethanol → 3-fluorodibenzo[b,e]oxepin-11(6H)-one

HRID 477778Notes

Reaction equation

HRID 477778 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.C(O)C.[F:18][C:19]1[CH:20]=[C:21]([O:25][CH2:26][C:27]2[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=2[C:29]([OH:31])=O)[CH:22]=[CH:23][CH:24]=1>O>[F:18][C:19]1[CH:24]=[CH:23][C:22]2[C:29](=[O:31])[C:28]3[CH:32]=[CH:33][CH:34]=[CH:35][C:27]=3[CH2:26][O:25][C:21]=2[CH:20]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14812Phosphorus oxide (P4O10)HCID 11791464HCID 11791464, compound

Product 1

HCID 110751573-fluorodibenzo[b,e]oxepin-11(6H)-oneYield 79.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To 250 g of phosphorus pentoxide is slowly added 160 ml of ethanol at room temperature. The mixture is further stirred with heating at 100° C. for 1 hour. Thereto 42 g of 2-[(3-fluorophenyloxy)methyl]benzoic acid is added and the mixture is stirred with heating at 100° C. for 1 hour. After cooling to room temperature, 500 ml of water is added. After extraction with toluene, washing successively with saturated sodium hydrogen carbonate, water and a saturated saline solution and drying over magnesium sulfate, the solvent is distilled off under reduced pressure to give 31 g of 3-fluoro-6,11-dihydrodibenz[b,e]oxepin-11-one (oil). Mass spectrum m/z: 228(M+).

Workup

  1. customat room temperature
  2. stirringthe mixture is stirred
  3. temperaturewith heating at 100° C. for 1 hour
  4. temperatureAfter cooling to room temperature
  5. extractionAfter extraction with toluene
  6. washwashing successively with saturated sodium hydrogen carbonate, water
  7. dry with materiala saturated saline solution and drying over magnesium sulfate
  8. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-cb5d18deb64a41ddb87a83b3376adff0
Source dataset
uspto-grants-1989_12
Patent number
US04889858

Reaction notes

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