Azobisisobutyronitrile → Diethyl (2-bromo-4-(bromomethyl)phenyl)(difluoro)methylphosphonate
Reaction equation
[CH2:1]([O:3][P:4]([C:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[Br:19])([F:11])[F:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[Br:20]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[CH2:6]([O:5][P:4]([C:9]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18][Br:20])=[CH:14][C:13]=1[Br:19])([F:11])[F:10])(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]Participants
5
Procedure
A solution of [(2-bromo-4-methyl-phenyl)-difluoro-methyl]-phosphonic acid diethyl ester (10.93 g, 30.6 mmol), N-bromosuccinimide (5.45 g, 30.6 mmol) and AIBN (100 mg) in benzene (300 mL) was refluxed for 18 h. The reaction mixture was concentrated in vacuo and redissolved in Ethyl acetate (200 mL). The solution was washed with H2O (50 mL), HCl (1 N, 50 mL), NaHCO3 (5%, 50 mL) and H2O (50 mL). The solvent was removed and the residue was purified by column chromatography on silica gel, eluting with hexanes/EtOAc (4:1) to provide a colorless oil (9.6 g, 80% purity with starting material as byproduct), which was taken on to the next step without further purification.
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutionredissolved in Ethyl acetate (200 mL)
- washThe solution was washed with H2O (50 mL), HCl (1 N, 50 mL), NaHCO3 (5%, 50 mL) and H2O (50 mL)
- customThe solvent was removed
- customthe residue was purified by column chromatography on silica gel
- washeluting with hexanes/EtOAc (4:1)
- customto provide a colorless oil (9.6 g, 80% purity with starting material as byproduct), which
- customwas taken on to the next step without further purification
Sources & evidence
- ORD record
- ord-f2e62de274634c9f8550344a028d6242
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07381736B2
Reaction notes
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