Sodium Azide → HCID 57426182, compound

HRID 220770Notes

Reaction equation

HRID 220770 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14]Br)=[C:10]([F:16])[CH:9]=1>CN(C=O)C.CCOC(C)=O>[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:1]=[N+:2]=[N-:3])=[C:10]([F:16])[CH:9]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 18766370Methyl 4-(bromomethyl)-3-fluorobenzoate

Product 1

HCID 57426182HCID 57426182, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium azide (609 mg) was added to a solution of 4-bromomethyl-3-fluorobenzoic acid methyl ester from Example E3.2 (2.1 g, 8.5 mmol) in DMF (30 ml). The mixture was stirred for 18 h, diluted with EtOAc, washed with water and brine and concentrated in vacuo to give a colourless oil identified as the title compound (1.8 g, 100%).

Workup

  1. washwashed with water and brine
  2. concentrationconcentrated in vacuo
  3. customto give a colourless oil

Sources & evidence

ORD record
ord-e9a6428177bc43d1a2905c16a88ea4c3
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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