Ethyl Bromide → HCID 20239562, compound

HRID 364653Notes

Reaction equation

[Mg].[CH2:2](Br)[CH3:3].[Cl:5][C:6]1[CH:28]=[CH:27][C:9]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:14][CH:13]=2)=[O:11])=[CH:8][CH:7]=1.[Cl-].[NH4+]>CCOCC>[Cl:5][C:6]1[CH:28]=[CH:27][C:9]([C:10]([CH2:2][CH3:3])([OH:11])[C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1

Participants

Conditions

Temperature: -30 °C

Procedure

To a Grignard reactant prepared from 7.2 g. of magnesium turnings and 32.6 g. of ethyl bromide in 120 ml. of dry ether a solution of 25.6 g. of 4-chloro-4'-[3-(diethylamino)-propoxy]-benzophenone in 300 ml. of dry ether is added dropwise, with stirring at -30° C. The reaction mixture is refluxed for 30 minutes. After cooling, it is poured onto a solution of ammonium chloride in ice water. The aqueous phase is extracted with ether, the ethereal phase is washed to neutral with water, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. Distillation of the residue in vacuo yields 15.3 g. of the title compound, boiling at 212° to 214° C./13.3 Pa.

Workup

temperatureThe reaction mixture is refluxed for 30 minutes
temperatureAfter cooling
extractionThe aqueous phase is extracted with ether
washthe ethereal phase is washed to neutral with water
dry with materialdried over anhydrous magnesium sulfate
customthe solvent is evaporated under reduced pressure
distillationDistillation of the residue in vacuo
customyields 15.3 g

Sources & evidence

ORD record: ord-295c275de3ad4009a7b9f416cc8c2ed3
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04605672

Reaction notes

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