Ammonium Chloride → 4-((5-Chloro-furan-2-yl)-hydroxy-methyl)-benzonitrile

HRID 1927250Notes

Reaction equation

I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C([Mg]Cl)(C)C.[Cl:15][C:16]1[O:20][C:19]([CH:21]=[O:22])=[CH:18][CH:17]=1.[Cl-].[NH4+]>C1COCC1>[Cl:15][C:16]1[O:20][C:19]([CH:21]([OH:22])[C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of THF (40 mL) and 4-iodobenzonitrile (2.0 g) was added isopropylmagnesium chloride (2M, 6.1 mL) dropwise at −78° C. under a nitrogen atmosphere, which was stirred for 1 hour and 10 minutes at 0° C. After cooling to 78° C., 5-chloro-2-furaldehyde (1.4 g) was added dropwise thereto, which was stirred for 15 minutes at room temperature. A saturated aqueous ammonium chloride solution was added at room temperature, and then extraction was performed with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered, after which the filtrate was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the titled compound (2.4 g).

Workup

temperatureAfter cooling to 78° C.
stirringwhich was stirred for 15 minutes at room temperature
extractionextraction
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customafter which the filtrate was evaporated under a reduced pressure
customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-43def14f3cb1465ea87a5d8ae23e90e1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183264B2

Reaction notes

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