Hydrochloric Acid → 1-[4′-(Acetyloxy)[1,1′-biphenyl]-4-yl]-2-bromoethanone

HRID 2183430Notes

Reaction equation

[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[Br:17][CH2:18][C:19](Br)=[O:20].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClCCl>[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:19](=[O:20])[CH2:18][Br:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 50 g (236 mmol) of [1,1′-biphenyl]-4-yl acetate in 500 ml dichloromethane was placed under argon and cooled to 0° C. Bromoacetyl bromide (31.6 ml, 363 mmol) was added, followed by aluminium chloride (94.3 g, 707 mmol) which was added in portions under vigorous stirring over 30 min. The resulting mixture was stirred at 0° C. for a further 30 min and at room temperature overnight. The mixture was then slowly poured into 500 ml of cold 10% HCl and extracted three times with dichloromethane. The organic layer was dried over Na2SO4, filtered and evaporated. The residue was triturated with 1:1 diisopropyl ether/isopropanol, filtered, and the remaining solid dried under vacuum.

Workup

additionwas added in portions
stirringThe resulting mixture was stirred at 0° C. for a further 30 min and at room temperature overnight
extractionextracted three times with dichloromethane
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
customevaporated
customThe residue was triturated with 1:1 diisopropyl ether/isopropanol
filtrationfiltered
customthe remaining solid dried under vacuum

Sources & evidence

ORD record: ord-e58deeee997e406b83f6e0b01b224aae
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06900194B1

Reaction notes

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