Nitrogen → HCID 86687927, compound

HRID 2401472Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([CH3:16])=[C:5]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7].C1C(=O)N([Br:24])C(=O)C1.N#N>CC#N.CC(N=NC(C#N)(C)C)(C#N)C>[Br:24][CH2:16][C:4]1[C:3]([O:2][CH3:1])=[C:12]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of methyl 3-methoxy-2-methyl-4-nitrobenzoate (800 mg, 3.6 mmol) in CH3CN (10 mL) was added NBS (770 mg, 4.3 mmol) and AIBN (12 mg, 0.072 mmol) under the protection of N2. The mixture was refluxed at 80° C. for overnight. After the solvent was evaporated in vacuo, the resulting residue was purified by silica gel-column (eluting with PE/EA=15:1) to afford methyl 2-(bromomethyl)-3-methoxy-4-nitrobenzoate as yellow oil (910 mg, yield 84%). m/z (ES+APCI)+: [M−Br]+224.1.

Workup

customAfter the solvent was evaporated in vacuo
customthe resulting residue was purified by silica gel-column (eluting with PE/EA=15:1)

Sources & evidence

ORD record: ord-facb1f807bcd41af9e9f3f1dc23eccc8
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796296B2

Reaction notes

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