2-Bromoanisole → 1-(4-Diethylcarbamoylphenyl)-1-(2-methoxyphenyl)methyl alcohol

HRID 895608Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH3:9].[Mg].[CH2:11]([N:13]([CH2:24][CH3:25])[C:14]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1)=[O:15])[CH3:12].[Cl-].[NH4+]>O1CCCC1>[CH2:24]([N:13]([CH2:11][CH3:12])[C:14]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]([OH:21])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH3:9])=[CH:18][CH:17]=1)=[O:15])[CH3:25]

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 2-bromoanisole (12.1 ml) dissolved in tetrahydrofuran (200 ml) was added with magnesium (2.368 g) and stirred at 60° C. for 1 hour to prepare a Grignard reagent. This Grignard reagent was added with a solution of 4-diethylcarbamoylbenzaldehyde (10.0 g) dissolved in tetrahydrofuran (200 ml) with ice cooling and stirred at room temperature for 1 hour. The reaction mixture was added with saturated aqueous ammonium chloride (400 ml) with ice cooling to quench the reaction and then extracted twice with dichloromethane (400 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:1) to obtain 14.14 g of the title compound. Yield: 93%.

Workup

stirringstirred at room temperature for 1 hour
customto quench
customthe reaction
extractionextracted twice with dichloromethane (400 ml)
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (elution solvent: hexane:ethyl acetate=1:1)

Sources & evidence

ORD record: ord-a017018e61b849f4889d7677c6837eb6
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916822B2

Reaction notes

Loading…