Thionyl Chloride → 2-[Chloro(cyclohexyl)methyl]-3-methyl-1-benzofuran-5-carbonitrile

HRID 2091156Notes

Reaction equation

[CH:1]1([CH:7](O)[C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:11]=3[C:12]=2[CH3:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:23])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:23][CH:7]([CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:11]=2[C:12]=1[CH3:13]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution (10 mL) of 2-[cyclohexyl(hydroxy)methyl]-3-methyl-1-benzofuran-5-carbonitrile (922 mg) synthesized above in toluene was added thionyl chloride (374 μL), and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was poured into ice-cooled saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (868 mg, 88%) as a pale-yellow solid.

Workup

additionThe reaction mixture was poured into ice-
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-ef9ed030a8c849e79e168eb6154af4ef
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08436043B2

Reaction notes

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