Trifluoroacetic anhydride → Methyl 11-oxo-6,11-dihydrodibenzo[b,e]oxepine-2-carboxylate

HRID 1196983Notes

Reaction equation

HRID 1196983 reaction equation
[K+].[Br-].[CH3:3][O:4][C:5]([C:7]1[CH:23]=[CH:22][C:10]([O:11][CH2:12][C:13]2[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=2[C:15]([OH:17])=O)=[CH:9][CH:8]=1)=[O:6].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[O:17]=[C:15]1[C:14]2[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=2[CH2:12][O:11][C:10]2[CH:22]=[CH:23][C:7]([C:5]([O:4][CH3:3])=[O:6])=[CH:8][C:9]1=2

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 253877Potassium BromideHCID 109790172-[(4-methoxycarbonylphenoxy)methyl]benzoic Acid

Product 1

HCID 2769045Methyl 11-oxo-6,11-dihydrodibenzo[b,e]oxepine-2-carboxylateYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

IR (KBr disk): 3400, 1700, 1610, 1260, 1235 cm-1The thus obtained 2-(4-methoxycarbonylphenoxy) methyl benzoic acid (392.7 g) is suspended in 5.0 l of methylene chloride and 266.0 g of trifluoroacetic anhydride is added thereto. After stirring the mixture at room temperature for one hour, 19.4 g of boron trifluoride-ethylether complex is added thereto and the mixture is stirred at room temperature for two hours. The reaction solution is poured into ice water. After an organic solvent layer is separated from the mixture, the organic layer is washed with diluted aqueous sodium hidroxide solution and water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 335.3 g of methyl 11-oxodibenz[b,e]oxepin-2-carboxylate as a white crystal.

Workup

  1. addition19.4 g of boron trifluoride-ethylether complex is added
  2. stirringthe mixture is stirred at room temperature for two hours
  3. customAfter an organic solvent layer is separated from the mixture
  4. washthe organic layer is washed with diluted aqueous sodium hidroxide solution and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2443d15f47b441889824c82f696a8c03
Source dataset
uspto-grants-1992_05
Patent number
US05116863

Reaction notes

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