Reaction #2139954

ord-8effeacce2064b4d81a75da8ac834529

Reaction equation

CCOc1ccc(Br)c(C(=O)Oc2c(Br)ccc(OCc3ccccc3)c2F)c1F
3-benzyloxy-6-bromo-2-fluorophenyl 6-bromo-3-ethoxy-2-fluorobenzoate
→
CCOc1ccc2c(c1F)c(=O)oc1c(F)c(OCc3ccccc3)ccc12
8-ethoxy-4,7-difluoro-3-benzyloxybenzo[c]chromen-6-one
Yield 21.0%

Reactants

CCOc1ccc(Br)c(C(=O)Oc2c(Br)ccc(OCc3ccccc3)c2F)c1F
3-benzyloxy-6-bromo-2-fluorophenyl 6-bromo-3-ethoxy-2-fluorobenzoate

Reagents

[Cu]
copper

Solvents

CN(C)C=O
DMF
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractionextracted with ethyl acetate
  2. 2
    Dryingthe combined extracts were dried over sodium sulfate
  3. 3
    Otherevaporated
  4. 4
    OtherCrystallisation of the crude product from THF

Procedure

103 g (0.188 mol) of 3-benzyloxy-6-bromo-2-fluorophenyl 6-bromo-3-ethoxy-2-fluorobenzoate were dissolved in 1 l of DMF and refluxed for 72 hours in the presence of 119 g (1.88 mol) of copper powder. The batch was subsequently diluted with water and extracted with ethyl acetate, and the combined extracts were dried over sodium sulfate and evaporated. Crystallisation of the crude product from THF gave 15 g (21% of theory) of 8-ethoxy-4,7-difluoro-3-benzyloxybenzo[c]chromen-6-one as pale-yellow crystals.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07326447B2uspto-grants-2008_02