Hydrofluoric Acid → Dimethyl 2-bromo-2-fluoropentane-1,5-dioate
Reaction equation
[FH:1].[Br:2]N1C(=O)CCC1=O.[N+](=[C:12]([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:13]([O:15][CH3:16])=[O:14])=[N-]>N1C=CC=CC=1.CCOCC>[Br:2][C:12]([F:1])([CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:13]([O:15][CH3:16])=[O:14]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a cold solution of 5 mL of 70% hydrogen fluoride in pyridine and 1.2 g (6.7 mmol) N-bromosuccinimide in 10 mL of ether is added a solution of dimethyl 2-diazopentane-1,5-dioate (1.1 g, 5.9 mmol) in ether (10 mL) at 0C. The mixture is stirred at 0° C. for 30 minutes The solution is washed with water (20 mL), brine (20 mL) and dried over sodium sulfate. The solvent is removed in vacuo to yield dimethyl 2-bromo-2-fluoropentane-1,5-dioate which can be further purified by column chromatography.
Workup
- washis washed with water (20 mL), brine (20 mL)
- dry with materialdried over sodium sulfate
- customThe solvent is removed in vacuo
Sources & evidence
- ORD record
- ord-f7cb93a87c6842cfa4a7fa5248a8b22d
- Source dataset
- uspto-grants-1999_02
- Patent number
- US05874448
Reaction notes
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