2-Chloro-6-nitrotoluene → 2-(Bromomethyl)-1-chloro-3-nitrobenzene

HRID 629972

Reaction equation

HRID 629972 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].C1C(=O)N([Br:19])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:11][C:3]1[C:4]([N+:8]([O-:10])=[O:9])=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 67402-Chloro-6-nitrotolueneHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide

Product 1

HCID 918582-(Bromomethyl)-1-chloro-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of the 1-chloro-2-methyl-3-nitrobenzene (2.0 g, 11.66 mmol) in anhydrous carbon tetrachloride 50 mL, NBS (2.07 g, 11.66 mmol) and benzoyl peroxide (0.141 g, 0.583 mmol) was added. The reaction mixture was heated to reflux overnight. Then, the reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated to provide crude 2-(bromomethyl)-1-chloro-3-nitrobenzene, which was used for the next step without any further purification (2.93 g); 1H NMR (400 MHz, DMSO-d6): δ 4.77 (s, 2H), 7.60 (t, J=6.2, 8.2 Hz, 1H), 7.90 (d, J=8.2 Hz, 1H), 8.00 (d, J=8.2 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux overnight
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-e1d5f5cba1a3427b8e0515b8d48e74a5
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Linked notes

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