Dimethylformamide → 6-Bromo-2-fluoro-3-propylbenzaldehyde

HRID 718482Notes

Reaction equation

[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH3:18])=[C:12]([F:19])[CH:11]=1.CN([CH:23]=[O:24])C>C1COCC1>[Br:9][C:10]1[C:11]([CH:23]=[O:24])=[C:12]([F:19])[C:13]([CH2:16][CH2:17][CH3:18])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: -70 °C

Procedure

Under a nitrogen atmosphere, LDA (50.7 mL, 56.25 mmol) was slowly added dropwise, at −70° C. or lower, to a THF (100 mL) solution of 4-bromo-2-fluoro-1-propylbenzene (50) (11.1 g, 51.13 mmol). The reaction mixture was agitated at −70° C. or lower for 1 hour, and then DMF (6.15 g, 76.70 mmol) was slowly added dropwise thereto. The reaction mixture was returned to room temperature, and then quenched with 100 mL of 1N hydrochloric acid aqueous solution, and extracted with 60 mL of toluene 3 times. Combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine, dried over magnesium sulfate and a solvent was distilled off by evaporator. The residue was purified by silica gel column chromatography, and thus 6-bromo-2-fluoro-3-propylbenzaldehyde (51) (5.0 g, yield 36%) was obtained.

Workup

customwas returned to room temperature
customquenched with 100 mL of 1N hydrochloric acid aqueous solution
extractionextracted with 60 mL of toluene 3 times
washCombined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate, water and saturated brine
dry with materialdried over magnesium sulfate
distillationa solvent was distilled off by evaporator
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-0f1cdce2f3b84a528713ea345a888ec4
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193908B2

Reaction notes

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