Dimethylformamide → 5-(1-Fluorocyclopropyl)-2-methoxybenzaldehyde

HRID 406398Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([C:13]2([F:16])[CH2:15][CH2:14]2)[CH:10]=[CH:9][C:8]=1[O:17][CH3:18].CN([CH:22]=[O:23])C.C(=O)(O)[O-].[Na+]>C1COCC1>[F:16][C:13]1([C:11]2[CH:10]=[CH:9][C:8]([O:17][CH3:18])=[C:7]([CH:12]=2)[CH:22]=[O:23])[CH2:15][CH2:14]1

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (2.7M solution in hexane, 3.42 ml) was added at −78° C. to a solution of 2-bromo-4-(1-fluorocyclopropyl)-1-methoxybenzene (1.88 g) in THF (62 ml), followed by addition of a solution of DMF (650 μl) in THF. After the reaction mixture was stirred at −78° C. for 30 minutes, a saturated aqueous solution of sodium bicarbonate was added to the reaction mixture and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (1.00 g).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over anhydrous magnesium sulfate
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-4375d25adb354f42be72c9add84c9f60
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754100B2

Reaction notes

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