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

HRID 576930

Reaction equation

HRID 576930 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-f2052cb3f42249e49d8094224a1c411f
Source dataset
uspto-grants-2015_05
Patent number
US09040538B2

Linked notes

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