HCID 20085919, compound → HCID 20085916, compound

HRID 1608469Notes

Reaction equation

HRID 1608469 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O>C(Cl)Cl.FC(F)(F)C(OC(=O)C(F)(F)F)=O>[Br:19][C:16]1[CH:17]=[CH:18][C:13]2[O:12][CH2:11][C:5]3[CH:4]=[CH:3][C:2]([Br:1])=[CH:10][C:6]=3[C:7](=[O:9])[C:14]=2[CH:15]=1

Participants

4

Reactant 1

HCID 20085919HCID 20085919, compound

Product 1

HCID 20085916HCID 20085916, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneCatalystHCID 9845Trifluoroacetic anhydrideSolvent

Procedure

A solution of 5-bromo-2-(4-bromophenoxymethyl)benzoic acid (100 g, 0.26 mole), and trifluoroacetic anhydride (160 mL) in one liter of methylene chloride containing 20 drops of boron trifluoride-ether complex was refluxed for three hours. The mixture was poured into ice water and then extracted with diethyl ether. Concentration of ether solution under reduced pressure and chromatography of the residue on a silica gel column (Waters Associates, Prep 500) with hexane/ethyl acetate (9:1) gave the ketone (45 g) mp 193°-194° C. pmr (DMSO-d6) δ: 8.12 (d, J=2.7 Hz, 1H, H4) , 7.27-7.91 (m, 4H, aromatic H) , 7.10 (d, J=8.8 Hz, 1H, H4), 5.32 (s, 2H, ArCH2O).

Workup

  1. extractionextracted with diethyl ether

Sources & evidence

ORD record
ord-5e2ca686f74145118d39be8a79d2bf37
Source dataset
uspto-grants-1995_03
Patent number
US05395610

Reaction notes

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