1-Bromomethyl-2,6-dichlorobenzene → 243118-22-1

HRID 424774Notes

Reaction equation

HRID 424774 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH2:4]Br.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C)C=O>[N:11]([CH2:4][C:3]1[C:2]([Cl:1])=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:10])=[N+:12]=[N-:13]

Participants

4

Reactant 2

HCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 33557Sodium Azide

Product 1

HCID 21282666243118-22-1Yield 87.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 2,6-dichlorobenzylbromide (0.50 g) in dimethylformamide (5 mL) is added sodium azide (0.41 g). The reaction is heated to 55° C. overnight. The resulting solution is cooled to room temperature and is concentrated under reduced pressure. The residue is dissolved in ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (0.37 g). 1H NMR (400 MHz, CDCl3) δ 7.45-7.40 (d, 2H), 7.30-7.25 (t, 1H), 4.73 (s, 2H).

Workup

  1. temperatureThe resulting solution is cooled to room temperature
  2. concentrationis concentrated under reduced pressure
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-42bbf5cb530d4db688b659a49f3e9095
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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