Sodium Azide → 4-(Azidomethyl)-1-bromo-2-fluorobenzene

HRID 2041453Notes

Reaction equation

HRID 2041453 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Br:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10]Br)=[CH:8][C:7]=1[F:14]>CN(C=O)C>[N:1]([CH2:10][C:9]1[CH:12]=[CH:13][C:6]([Br:5])=[C:7]([F:14])[CH:8]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 116661761-Bromo-4-(bromomethyl)-2-fluorobenzene

Product 1

HCID 576561344-(Azidomethyl)-1-bromo-2-fluorobenzeneYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Add sodium azide (2.912 g, 44.8 mmol) to a solution of 4-bromo-3-fluorobenzyl bromide (6 g, 22.4 mmol) in anhydrous DMF (127 mL) at room temperature under nitrogen. Heat the mixture at 90° C. for 1 h. Concentrate in vacuo and partition the residue between water and EtOAc. Extract the aqueous phase twice with EtOAc. Wash the combined organics extracts with iced-water. Dry the organic layer over Na2SO4, filter and concentrate in vacuo to obtain the desired intermediate as a solid (4.92 g, 96%).

Workup

  1. concentrationConcentrate in vacuo
  2. custompartition the residue between water and EtOAc
  3. extractionExtract the aqueous phase twice with EtOAc
  4. washWash the combined
  5. dry with materialDry the organic layer over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-494ba272bb6544e18da9610c5f56df64
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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