Pyridine, hydrofluoride (1:1) → HCID 19019910, compound

HRID 1109829Notes

Reaction equation

HRID 1109829 reaction equation
[Cl:1][C:2]1[CH2:3][C:4]([C:12]([O:14][CH3:15])=[O:13])=[C:5]([CH2:10][CH:11]=1)[C:6]([O:8][CH3:9])=[O:7].C1C=CN=CC=1.[FH:22].[Br:23]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:23][CH:11]1[CH2:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH2:3][C:2]1([Cl:1])[F:22]

Participants

6

Reactant 4

HCID 64774Pyridine, hydrofluoride (1:1)HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 19019908HCID 19019908, compound

Product 1

HCID 19019910HCID 19019910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dimethyl 4-chloro-3,6-dihydrophthalate (0.19 g) and pyridinium poly(hydrogen fluoride) were mixed together at room temperature and N-bromosuccinimide was slowly added. The reaction mixture turned dark then light yellow. After stirring at room temperature for 3 hours, the reaction mixture was carefully poured into saturated sodium bicarbonate solution containing methylene chloride. The methylene chloride layer was dried with magnesium sulfate and the solvent removed under reduced pressure. NMR and GC-MS analysis of the reaction mixture revealed the major product to be the desired dimethyl 5-bromo-4-chloro-4-fluoro-3,4,5,6-tetrahydrophthalate along with some dimethyl 4-fluorophthalate.

Workup

  1. dry with materialThe methylene chloride layer was dried with magnesium sulfate
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-5ecb077cbedd4c7fb548de2d407fda26
Source dataset
uspto-grants-1994_06
Patent number
US05322954

Reaction notes

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