Potassium Carbonate → N-(2-bromo-5-nitrophenyl)-N-(2-methylprop-2-en-1-yl)acetamide

HRID 74055

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

At 25° C., a solution of 3-bromo-2-methylpropene (3.4 g, 55.6 mmol) in anhydrous DMF (30 mL) was added dropwise to a solution of N-(2-bromo-5-nitrophenyl)acetamide (3.6 g, 13.9 mmol) and potassium carbonate (3.9 g, 27.8 mmol) in anhydrous DMF (50 mL). The reaction mixture was stirred at 25° C. overnight. The reaction mixture was then filtered and the filtrate was treated with sat. Na2CO3 solution. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried over MgSO4, filtered and concentrated under vacuum to provide N-(2-bromo-5-nitrophenyl)-N-(2-methylprop-2-enyl)acetamide as a golden solid (3.1 g, 85%). ESI-MS 313 m/z (MH+).

Workup

filtrationThe reaction mixture was then filtered
additionthe filtrate was treated with sat. Na2CO3 solution
customThe organic layer was separated
extractionthe aqueous layer was extracted with EtOAc
washThe combined organic extracts were washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-252a44ef5fe044feb5c56887c93dee3d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829204B2

Linked notes

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