Sulfuric Acid → tert-Butyl 2,4-dibromobutyrate

HRID 1396838Notes

Reaction equation

HRID 1396838 reaction equation
[Br:1][CH:2]([CH2:6][CH2:7][Br:8])[C:3]([OH:5])=[O:4].[CH3:9][C:10](O)([CH3:12])[CH3:11].OS(O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:1][CH:2]([CH2:6][CH2:7][Br:8])[C:3]([O:5][C:10]([CH3:12])([CH3:11])[CH3:9])=[O:4]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 10340Sodium CarbonateHCID 129406012,4-Dibromobutanoic acid

Product 1

HCID 5107723tert-Butyl 2,4-dibromobutyrateYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

2,4-Dibromobutanoic acid (the crude product from above) dissolved in DCM (10 L) in a 50 L-reactor. 2-Methylpropan-2-ol (12000 g, 162.16 mol) and boron anhydride (8000 g, 114.29 mol) were added to the above solution. 1680 g of H2SO4 was added dropwise to the above solution under N2 (gas) while maintaining the temperature at room temperature (25-30° C.). The mixture was allowed to react for 24 h at room temperature. Then 15 L aqueous Na2CO3 (sat.) was added to quench the reaction. The organic phase was separated and dried over Na2SO4. The solvent was removed under vacuum to give the crude product, which was purified by silica gel column chromatography to give tert-butyl 2,4-dibromobutanoate as a brown oil (3800 g, 12.58 mol, 39%).

Workup

  1. customto react for 24 h at room temperature
  2. customto quench
  3. customthe reaction
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under vacuum
  7. customto give the crude product, which
  8. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9cdd6d4a63e0442bb25478cb41ea6d86
Source dataset
uspto-grants-2014_12
Patent number
US08901119B2

Reaction notes

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