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

HRID 458075Notes

Reaction equation

HRID 458075 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-d91a73f3b1034c968862d7e825b9005b
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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