Lithium Bromide → 2-Isobutyl-succinic acid-4-t-butyl ester

HRID 722906Notes

Reaction equation

HRID 722906 reaction equation
[Br-].[Li+].C[O:4][C:5](=[O:19])[CH:6]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>CC(C)=O>[C:11]([O:10][C:8](=[O:9])[CH2:7][CH:6]([CH2:15][CH:16]([CH3:17])[CH3:18])[C:5]([OH:19])=[O:4])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 218883142-Isobutylsuccinic acid-4-t-butyl ester-1-methyl ester

Product 1

HCID 99427122-Isobutyl-succinic acid-4-t-butyl esterYield 97.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Anhydrous lithium bromide (25 g, 287.3 mmol) was added to a stirring mixture of 2 (15.84 g, 57.4 mmol) in acetone (150 mL) under argon, and the mixture was refluxed for 2 hours. After cooling, the acetone was evaporated under reduced pressure, and the residue was taken up in ether (100 mL), washed with water (100 mL), brine, dried (MgSO4), and the solvent was evaporated under reduced pressure to give the dibromide 3 (13.5 g, 55.8 mmol, 97%) as an orange liquid; δH (400 MHz; CDCl3): 3.5 (4H, m), 2.45 (2H, m), 2.05 (2H, m), 1.6 (2H, m).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. customthe acetone was evaporated under reduced pressure
  4. washwashed with water (100 mL), brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-403894a390dd432daa4f38672169fbbb
Source dataset
uspto-grants-2006_11
Patent number
US07138542B2

Reaction notes

Loading…