4-bromo-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one → 4-azido-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one

HRID 1696335Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

4-Bromo-6-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1(2H)-one (3.9 g, 14 mmol) was added to DMF (10 mL) followed by azidosodium (3.6 g, 55 mmol). The mixture was heated to 60° C. overnight. The reaction was cooled to RT and quenched with water (25 mL). The aqueous layer was extracted with Et2O (3×100 mL). The combined organic layers were washed with brine, dried over MgSO4 and filtered. The solvent was evaporated and the residue was purified by column chromatography (0-50% EtOAc/Hexane to provide the title compound as a white solid (3.05 g, 90% yield). MS m/z: 268.2 (M+Na).

Workup

temperatureThe reaction was cooled to RT
customquenched with water (25 mL)
extractionThe aqueous layer was extracted with Et2O (3×100 mL)
washThe combined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
customThe solvent was evaporated
customthe residue was purified by column chromatography (0-50% EtOAc/Hexane

Sources & evidence

ORD record: ord-24dbf30c4c494c088d2bcc6fba81703f
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163766B2

Reaction notes

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