Ethanol → Benzoic acid, 2,4,5-trifluoro-3-methoxy-, ethyl ester

HRID 729362

Reaction equation

[F:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([F:13])[C:8]([F:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15](Cl)(=O)[C:16](Cl)=O.C(O)C.C([O-])(O)=O.[Na+]>ClCCl.CN(C)C=O>[CH2:15]([O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([F:14])[C:9]([F:13])=[C:10]([O:11][CH3:12])[C:2]=1[F:1])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2,4,5-trifluoro-3-methoxybenzoic acid (2.513 g, 12.19 mmol) in dichloromethane (50 mL) at 0° C. is treated with oxalyl chloride (5.4 mL, 61.9 mmol) followed by N,N-dimethylformamide (4 drops). The mixture is stirred at 0° C. for 5 minutes and then at room temperature for 2.5 hours. The mixture is concentrated to near dryness and then co-evaporated from benzene. The resulting acid chloride is diluted with dichloromethane (50 mL), cooled to 0° C., and then anhydrous ethanol (7.30 mL, 124 mmol) is added dropwise. The resulting solution is stirred at room temperature for 4.5 hours, poured into saturated NaHCO3 solution, and extracted with dichloromethane. The combined organic extracts are washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to afford the title compound as a light yellow liquid (2.82 g). 1H NMR (CDCl3): δ 7.47 (ddd, 1H), 4.39 (q, 2H), 4.05 (s, 3H), 1.40 (t, 3H).

Workup

waitat room temperature for 2.5 hours
concentrationThe mixture is concentrated
additionThe resulting acid chloride is diluted with dichloromethane (50 mL)
temperaturecooled to 0° C.
stirringThe resulting solution is stirred at room temperature for 4.5 hours
extractionextracted with dichloromethane
washThe combined organic extracts are washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-276df7c94fad4fc6a9035df569eaef47
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582627B2

Linked notes

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