HCID 20085919, compound → HCID 20085916, compound

HRID 1463184Notes

Reaction equation

HRID 1463184 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, H10), 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-6208628588324da9b0d1ea41f04e1ac3
Source dataset
uspto-grants-1994_04
Patent number
US05300282

Reaction notes

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