Hydrofluoric Acid → Dimethyl 2-bromo-2-fluoropentane-1,5-dioate

HRID 618698Notes

Reaction equation

HRID 618698 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

HCID 14917Hydrofluoric AcidHCID 67184N-bromobutanimideHCID 54067448HCID 54067448, compound

Product 1

HCID 21847921Dimethyl 2-bromo-2-fluoropentane-1,5-dioate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Part B. 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 0° C. 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

  1. washis washed with water (20 mL), brine (20 mL)
  2. dry with materialdried over sodium sulfate
  3. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-486b68c166454e359cbe9b3f01a3e8ce
Source dataset
uspto-grants-1999_09
Patent number
US05955476

Reaction notes

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