Hydrochloric Acid → 3-(2-Methoxybenzoyl)benzonitrile

HRID 1087715Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Mg].II.[C:13]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](Cl)=[O:19])#[N:14].Cl>O1CCCC1>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:18]([C:17]1[CH:16]=[C:15]([CH:23]=[CH:22][CH:21]=1)[C:13]#[N:14])=[O:19]

Participants

Conditions

Temperature: -75 °C

Procedure

30 g (0.16 mol) of 2-bromoanisole are added dropwise to a mixture of 3.85 g (0.16 mol) of magnesium, containing a crystal of iodine, in 75 ml of anhydrous tetrahydrofuran and the reaction mixture is then refluxed for 1 hour. The resulting solution is then added dropwise to a solution of 26.48 g (0.16 mol) of 3-cyanobenzoyl chloride in 75 ml of anhydrous tetrahydrofuran, cooled to -75° C. The temperature is allowed to rise to 20° C., the reaction medium is hydrolyzed with a 1N aqueous solution of hydrochloric acid and the expected product is then extracted with ethyl acetate. The organic phase obtained is washed with water, dried over magnesium sulfate and then evaporated under reduced pressure. 30 g of the expected product (yield: 80%) are obtained in the form of crystals.

Workup

customto rise to 20° C.
extractionthe expected product is then extracted with ethyl acetate
customThe organic phase obtained
washis washed with water
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-c6caa68a70fd4db3b92c9fa4ade70935
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04960758

Reaction notes

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