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

HRID 887575Notes

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 NaH (2 g) (95% powder) in 100 mL anhydrous DMF was cooled to −78° C., and N-(2-bromo-5-nitrophenyl)acetamide (7 g) in 50 mL dry DMF was added to the mixture under N2. 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. 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 a yellow gum. MS: 314 (M+1). Calc'd. for C12H13BrN2O3—313.1.

Workup

temperatureAfter the mixture was warmed to 0° C.
additionThe 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
customEtOAc to afford a yellow gum

Sources & evidence

ORD record: ord-14906f402e0841018572d01e145b4792
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08247430B2

Reaction notes

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