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

HRID 458073Notes

Reaction equation

HRID 458073 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 95.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Anhydrous lithium bromide (10.6 g, 121.8 mmol) was added to a stirring mixture of 2 (5.95 g, 24.4 mmol) in acetone (50 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 (50 mL), washed with water (50 mL), brine, dried (MgSO4), and the solvent was evaporated under reduced pressure. The residue was chromatographed (SiO2, heptane/ethyl acetate, 95:5) to give the dibromide 3 (5.36 g, 86%) as an orange liquid; Rf(heptane-ethyl acetate, 8:2), 0.82. δH (400 MHz; CDCl3): 3.6 (2H, m), 3.45 (2H, m), 2.85 (2H, m), 2.1 (2H, m), 1.7 (2H, m; δc(400 MHz; CDCl3): 39.70, 33.79, 23.95.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. customthe acetone was evaporated under reduced pressure
  4. washwashed with water (50 mL), brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was chromatographed (SiO2, heptane/ethyl acetate, 95:5)

Sources & evidence

ORD record
ord-37b02f9e5de84c629a758513b289c411
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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