Sodium hydride → N-(2-bromo-5-nitrophenyl)-N-(2-methylprop-2-en-1-yl)acetamide

HRID 557360Notes

Reaction equation

[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[NH:13][C:14](=[O:16])[CH3:15].Br[CH2:18][C:19]([CH3:21])=[CH2:20]>CN(C=O)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[N:13]([CH2:20][C:19]([CH3:21])=[CH2:18])[C:14](=[O:16])[CH3:15]

Participants

Conditions

Temperature: -78 °C

Procedure

A suspension of 2 g NaH (95% powder) in anhydrous DMF (100 mL) was cooled to −78° C., N-(2-bromo-5-nitrophenyl)acetamide (7 g, Step A) in dry DMF (50 mL) was added to the mixture under N2 atmosphere. After the mixture was warmed to 0° C., 3-bromo-2-methylpropene (7.3 g in 20 dry DMF) was added to the mixture. The mixture was stirred at RT overnight. Next morning, the mixture was poured into a container of ice and extracted between saturated NaHCO3 solution and EtOAc. The resulting organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel with 7:2 hexane:EtOAc to afford the title compound as a yellow gum. MS: 314 (M+1). Calc'd. for C12H13BrN2O3−313.15.

Workup

temperatureAfter the mixture was warmed to 0° C.
additionNext morning, the mixture was poured into a container of ice
extractionextracted between saturated NaHCO3 solution and EtOAc
dry with materialThe resulting organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by flash chromatography on silica gel with 7:2 hexane

Sources & evidence

ORD record: ord-ad1c0deecdd6486d91c1454149f213e5
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058445B2

Reaction notes

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