Dimethylformamide → 2-Formyl-5-(trifluoromethyl)benzoic acid

HRID 78547Notes

Reaction equation

C([Li])CCC.CCCCCC.Br[C:13]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16].CN(C)[CH:28]=[O:29].[Cl-].[NH4+].C([O-])(O)=O.[Na+]>O1CCCC1>[CH:28]([C:13]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16])=[O:29]

Participants

Conditions

Temperature: -78 °C

Procedure

To a 250 mL round-bottomed flask, was added 2.5 M n-butyllithium/hexane (8.92 mL, 22.30 mmol) in tetrahydrofuran (40 mL) and cooled to −78° C., followed by dropwise addition of 2-bromo-5-(trifluoromethyl)benzoic acid (3 g, 11.15 mmol) in tetrahydrofuran (20 mL). After 30 min N,N-dimethylformamide (0.978 g, 13.38 mmol) was added and the solution slowly allowed to warm to rt. To the reaction was added saturated ammonium chloride solution, followed by addition of saturated NaHCO3 solution until basic. The aqueous layer was separated, and 2 N HCl was added until acidic. The mixture was extracted with ethyl acetate (3×20 mL). The organic layers were combined, dried, filtered, and concentrated. The resulting solid was used without further purification. MS (DCI/NH3) m/z 512 (M+NH4)+.

Workup

temperatureto warm to rt
customThe aqueous layer was separated
addition2 N HCl was added until acidic
extractionThe mixture was extracted with ethyl acetate (3×20 mL)
customdried
filtrationfiltered
concentrationconcentrated
customThe resulting solid was used without further purification

Sources & evidence

ORD record: ord-260dfd8883744abcb6e31cdf43accc51
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841334B2

Reaction notes

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