HCID 58687470, compound → HCID 58687478, compound

HRID 2052772Notes

Reaction equation

HRID 2052772 reaction equation
Br[C:2]1[C:7]([C:8]([O:10][C:11]2[C:16](Br)=[CH:15][CH:14]=[C:13]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]=2[F:26])=[O:9])=[C:6]([F:27])[C:5]([O:28][CH2:29][CH3:30])=[CH:4][CH:3]=1>CN(C=O)C.O.[Cu]>[CH2:29]([O:28][C:5]1[CH:4]=[CH:3][C:2]2[C:16]3[C:11](=[C:12]([F:26])[C:13]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:14][CH:15]=3)[O:10][C:8](=[O:9])[C:7]=2[C:6]=1[F:27])[CH3:30]

Participants

5

Reactant 1

HCID 58687470HCID 58687470, compound

Product 1

HCID 58687478HCID 58687478, compoundYield 21%

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

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.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined extracts were dried over sodium sulfate
  3. customevaporated
  4. customCrystallisation of the crude product from THF

Sources & evidence

ORD record
ord-8effeacce2064b4d81a75da8ac834529
Source dataset
uspto-grants-2008_02
Patent number
US07326447B2

Reaction notes

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