Carbon Tetrachloride → 1-Nitro-3-chloro-4-trichloromethylbenzene

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1C.[C:12]([Cl:16])(Cl)([Cl:14])[Cl:13]>>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]([C:12]([Cl:16])([Cl:14])[Cl:13])=[C:2]([Cl:1])[CH:7]=1)([O-:10])=[O:9]

Participants

Reactant 2

HCID 5943Carbon Tetrachloride

HCID 84912-Chloro-4-nitrotoluene

Product 1

HCID 205421641-Nitro-3-chloro-4-trichloromethylbenzeneYield 99.2%

Procedure

2-Chloro-4-nitrotoluene (2.19 g, 0.0128 mole) and dichloride monoxide (4.46 g, 0.0513 mole) in carbon tetrachloride (50 ml) were heated at 75°/18 hrs following the procedure described in Example 6. The product was dried and the solvent removed to give 1-nitro-3-chloro-4-trichloromethylbenzene (3.49 g, purity by HPLC 99.40%, yield 99.2%) as a pale yellow oil. The product was distikled in a short path still (bp 82-85/2μ) to give a pale yellow oil.

Workup

customThe product was dried
customthe solvent removed

Sources & evidence

ORD record: ord-59e8c79b6871488db9c0e5cfc92c84a0
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04226783

Reaction notes

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