Sodium Azide → 2-(Azidomethyl)-1,3-difluorobenzene

HRID 1927190Notes

Reaction equation

HRID 1927190 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([F:10])[C:3]=1[CH2:4]Br.[N-:11]=[N+:12]=[N-:13].[Na+].[N-]=[N+]=[N-]>O>[N:11]([CH2:4][C:3]1[C:2]([F:1])=[CH:9][CH:8]=[CH:7][C:6]=1[F:10])=[N+:12]=[N-:13]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 33558Azide2×HCID 5814352-(Bromomethyl)-1,3-difluorobenzene

Product 1

HCID 108883232-(Azidomethyl)-1,3-difluorobenzeneYield 93.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 250 ml round bottom flask, 2,6-difluorobenzylbromide (0.024 mol, 5 g), sodium azide (0.026 mol, 1.72 g) and water (50 ml) were charged. The reaction mixture was heated to 70° C. to 75° C. for 30 hours and formation of azide intermediate (99.4%) was monitored by gas chromatography. After completion of the reaction, the contents were cooled to room temperature. The layers of the reaction mixture were separated to obtain an upper water layer and a lower azide intermediate layer. The lower layer was then concentrated and dried under vacuum to obtain 3.8 g of the product.

Workup

  1. temperatureThe reaction mixture was heated to 70° C. to 75° C. for 30 hours
  2. customAfter completion of the reaction
  3. customThe layers of the reaction mixture were separated
  4. customto obtain an upper water layer
  5. concentrationThe lower layer was then concentrated
  6. customdried under vacuum

Sources & evidence

ORD record
ord-8a71067f756a4d0192e9a92aec097fe0
Source dataset
uspto-grants-2012_05
Patent number
US08183269B2

Reaction notes

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