Benzoic acid, 2,6-difluoro-, ethyl ester → Ethyl 2-fluoro-6-[3,4-(methylenedioxy)phenoxy]benzoate

HRID 1600851Notes

Reaction equation

F[C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:14]1[O:23][C:22]2[CH:21]=[CH:20][C:18]([O-:19])=[CH:17][C:16]=2[O:15]1.[Na+]>CS(C)=O.O>[F:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:2]([O:19][C:18]2[CH:20]=[CH:21][C:22]3[O:23][CH2:14][O:15][C:16]=3[CH:17]=2)[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

Conditions

Temperature: 50 °C

Procedure

Ethyl 2,6-difluorobenzoate (558 mg, 3.0 mmol) was added to dry sodium 3,4-methylenedioxyphenoxide (3.0 mmol, prepared as described in part A) in DMSO followed by addition of dry DMSO (2 ml). The reaction mixture was warmed to 50° C. forming a solution which turned from brown to green upon further heating. After 90 min., the reaction was cooled to 25° C., diluted with water (10 ml) and extracted with EtOAc (3×10 ml). The organic extract was washed with water (2×7 ml) and brine (7 ml), dried (MgSO4) and concentrated to give a light yellow oil. The product was purified by flash chromatography on SiO2 (5-20% EtOAc/hexane) yielding 532 mg of ethyl 2-fluoro-6-[3,4-(methylenedioxy)phenoxy]benzoate as a colorless oil (58% yield).

Workup

customprepared
customforming a solution which
temperaturethe reaction was cooled to 25° C.
extractionextracted with EtOAc (3×10 ml)
extractionThe organic extract
washwas washed with water (2×7 ml) and brine (7 ml)
dry with materialdried (MgSO4)
concentrationconcentrated
customto give a light yellow oil
customThe product was purified by flash chromatography on SiO2 (5-20% EtOAc/hexane)

Sources & evidence

ORD record: ord-a2f9bb1e35b243158f1e4eba34698378
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977117

Reaction notes

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