Hydrochloric Acid → 2-(4-Bromophenyl)-1-(2,4-dichlorophenyl)ethanone

HRID 2246696Notes

Reaction equation

[Na].C[Si](C)(C)N[Si](C)(C)C.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19]([OH:21])=O)=[CH:14][CH:13]=1.[Cl:22][C:23]1[CH:32]=[C:31]([Cl:33])[CH:30]=[CH:29][C:24]=1C(OC)=O.Cl>C1COCC1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C:19]([C:30]2[CH:29]=[CH:24][C:23]([Cl:22])=[CH:32][C:31]=2[Cl:33])=[O:21])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: -70 °C

Procedure

436 ml of a 2M solution of the sodium salt of hexamethyldisilazane in THF are cooled to −60° C., under a nitrogen atmosphere, 400 ml of THF are added, followed dropwise by a solution of 75 g of 4-bromophenylacetic acid in 100 ml of THF and the medium is left for 1 hour 30 minutes with stirring at −70° C. 67.9 g of methyl 2,4-dichlorobenzoate are then added dropwise, the medium is left for 30 minutes, with stirring, and then the temperature is allowed to rise to 5° C. The reaction mixture is poured over an ice/1 liter of 2N HCl mixture, extracted with ether, the organic phase is washed with a saturated NaHCO3 solution, with water, dried over Na2SO4 and the solvent is evaporated under vacuum to a volume of 200 ml, pentane is added and the crystallized product formed is drained. 80 g of the expected compound are obtained.

Workup

waitthe medium is left for 30 minutes
stirringwith stirring
customto rise to 5° C
extractionextracted with ether
washthe organic phase is washed with a saturated NaHCO3 solution, with water
dry with materialdried over Na2SO4
customthe solvent is evaporated under vacuum to a volume of 200 ml, pentane
additionis added
customthe crystallized product formed

Sources & evidence

ORD record: ord-2a95c07c8e934eda8370966cd05e7993
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07687537B2

Reaction notes

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