Nitric Acid → 5-Bromo-1,3-dimethoxy-2-nitrobenzene

HRID 2067828Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>C(OC(=O)C)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH3:11])[C:5]([N+:12]([O-:14])=[O:13])=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1-Bromo-3,5-dimethoxybenzene (10.9 g, 50 mmol) was dissolved in 100 mL of acetic anhydride and cooled to 0° C. A cooled solution of 70% HNO3 (6.4 mL, 100 mmol) in 20 mL of acetic anhydride was added dropwise and the resulting mixture was stirred for 1 hour at 0° C. and for 3 hours at room temperature. The reaction mixture was poured into ice-water with strong stirring and the yellow solid was filtered and washed with water. The solid as a mixture of two isomers was separated by silica gel column (ISCO, hexane/EtOAc, 0-30%, 40 min) to give 3.3 g (25%) of pure 5-bromo-1,3-dimethoxy-2-nitro-benzene as an yellow solid. 1H-NMR (DMSO-d6, 400 MHz): δ 7.17 (s, 2H), 3.89 (s, 6H).

Workup

stirringwith strong stirring
filtrationthe yellow solid was filtered
washwashed with water
additionThe solid as a mixture of two isomers
customwas separated by silica gel column (ISCO, hexane/EtOAc, 0-30%, 40 min)

Sources & evidence

ORD record: ord-aac207a83682480284743a3b765a6e97
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293911B2

Reaction notes

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