Sodium Azide → 1-(Azidomethyl)-4-fluoro-2-iodobenzene
Reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[I:10].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C>[N:11]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[I:10])=[N+:12]=[N-:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A suspension of 1-(bromomethyl)-4-fluoro-2-iodobenzene (15.68 g, 47.8 mmol) and sodium azide (4.21 g, 64.7 mmol) in dry DMF (30 mL) was heated to 50° C. for six hours. The reaction was filtered and the filtrate was concentrated in vacuo to a volume of about 10 mL. The crude was purified by flash column chromatography (ISCO column, 110 g silica gel) eluting with 100% hexane to afford the desired product as a clear oil.
Workup
- filtrationThe reaction was filtered
- concentrationthe filtrate was concentrated in vacuo to a volume of about 10 mL
- customThe crude was purified by flash column chromatography (ISCO column, 110 g silica gel)
- washeluting with 100% hexane
Sources & evidence
- ORD record
- ord-ef3627cca055460b918fa692e04cb783
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07323460B2
Reaction notes
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