Water → 2-(Azidomethyl)-1,3-difluorobenzene

HRID 335510Notes

Reaction equation

HRID 335510 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4]Cl.[N-:11]=[N+:12]=[N-:13].[Na+].O.C1CCCCC1>CS(C)=O>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4][N:11]=[N+:12]=[N-:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8078CyclohexaneHCID 33557Sodium AzideHCID 5815702,6-Difluorobenzyl chloride

Product 1

HCID 108883232-(Azidomethyl)-1,3-difluorobenzeneYield 100.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
22.5 °C

Procedure

A solution of 0.200 g (1.23 mmol) of 2,6-difluorobenzyl chloride in 0.5 mL of DMSO was added dropwise to a mixture of 0.090 g (1.23 mmol) of NaN3 in 2 mL of DMSO at 20-25° C. The reaction was left stirring at 20-25° C. during 4 h. until showing completion by TLC. The crude was treated with 1.6 mL of water and 1.6 mL of cyclohexane and the organic phase was vacuum distilled to obtain 0.210 g (97%) of 2,6-difluorobenzyl azide as yellowish oil

Workup

  1. waitThe reaction was left
  2. distillationdistilled

Sources & evidence

ORD record
ord-faa2385547d74a3e9828062d2569b01b
Source dataset
uspto-grants-2014_11
Patent number
US08884026B2

Reaction notes

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