Ethylene Glycol → 2-(6-Fluoro-3',5'-dimethoxy-4-nitrobiphenyl-3-yl)-1,3-dioxolane

HRID 56464Notes

Reaction equation

[F:1][C:2]1[C:7]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:17])[CH:9]=2)=[CH:6][C:5]([CH:18]=[O:19])=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:34](O)[CH2:35][OH:36]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[C:7]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:17])[CH:9]=2)=[CH:6][C:5]([CH:18]2[O:36][CH2:35][CH2:34][O:19]2)=[C:4]([N+:20]([O-:22])=[O:21])[CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 6-fluoro-3′,5′-dimethoxy-4-nitrobiphenyl-3-carbaldehyde (1.7 g, 5.6 mmol) and 4-toluenesulfonic acid (95.8 mg, 0.6 mmol) in 1,2-ethanediol (4.3 mL) and toluene (60 mL) was heated at 130° C. for 3 hours. After that, the reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), and washed by water (100 mL*3) and brine (100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=8/1 to 5/1) to afford the title compound (1.8 g, 89%) as a yellow solid. MS (ES+) C17H16FNO6 requires: 349, found: 350 [M+H]+.

Workup

temperatureAfter that, the reaction mixture was cooled to room temperature
washwashed by water (100 mL*3) and brine (100 mL)
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=8/1 to 5/1)

Sources & evidence

ORD record: ord-c6f276dd4f824154ad8a2db40e6ab5e4
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434700B2

Reaction notes

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