Carbon Dioxide → HCID 4771143, compound

HRID 2174154Notes

Reaction equation

[CH2:1]([O:5][C:6]1[C:11]([F:12])=[C:10]([F:13])[CH:9]=[C:8]([F:14])[C:7]=1[F:15])[CH2:2][CH2:3][CH3:4].C([Li])CCC.CCCCCC.[C:27](=[O:29])=[O:28].Cl>O1CCCC1>[CH2:1]([O:5][C:6]1[C:7]([F:15])=[C:8]([F:14])[C:9]([C:27]([OH:29])=[O:28])=[C:10]([F:13])[C:11]=1[F:12])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

24.4 g of the compound (2) dissolved in 250 mL of tetrahydrofuran (THF) were cooled at −78° C. in an argon atmosphere; thereto were then dripped 82 mL of a 1.6 M/L n-butyllithium/hexane solution, with stirring for 2 hours at the same temperature. After addition of a suitable amount of crushed dry ice, the temperature was raised to room temperature, followed by stirring overnight. 200 mL of 3N hydrochloric acid were then added under ice cooling, the organic layer was separated, and the aqueous layer was extracted with diethyl ether. The organic layers were combined, were washed with saturated brine, and were then dried over anhydrous magnesium sulfate. After evaporating the solvent, the organic layer was recrystallized from hexane to yield 14.6 g (54.8 mmol) of 4-butoxy-2,3,5,6-tetrafluorobenzoic acid (3).

Workup

temperaturethe temperature was raised to room temperature
stirringby stirring overnight
customthe organic layer was separated
extractionthe aqueous layer was extracted with diethyl ether
washwere washed with saturated brine
dry with materialwere then dried over anhydrous magnesium sulfate
customAfter evaporating the solvent
customthe organic layer was recrystallized from hexane

Sources & evidence

ORD record: ord-2c07fe339dce4b97b26e7eefa8cca5cf
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09059410B2

Reaction notes

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