Sodium Azide → 4-Azidomethyl-3-fluorobenzoic acid methyl ester
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]=1Participants
5
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
- washwashed with water and brine
- concentrationconcentrated in vacuo
- 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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