tert-Butanol → Tert-butyl 3-bromobutanoate

HRID 2167903Notes

Reaction equation

HRID 2167903 reaction equation
[Br:1][CH:2]([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:21](O)([CH3:24])([CH3:23])[CH3:22]>O1CCCC1>[C:21]([O:5][C:4](=[O:6])[CH2:3][CH:2]([Br:1])[CH3:7])([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 9845Trifluoroacetic anhydrideHCID 1028603-Bromobutanoic acid

Product 1

HCID 57092335Tert-butyl 3-bromobutanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The required 3-bromobutyric acid tert-butyl ester was prepared as follows: To a solution of 3-bromobutyric acid (5.0 mL; 47.0 mmol) in tetrahydrofuran (50 mL) was added dropwise trifluoroacetic anhydride (13.7 mL; 98.7 mmol) at −40° C. After 1 hour at −40° C. tert-butyl alcohol (20 mL) was added. The resulting mixture was allowed to warm to RT and stirred overnight. Subsequently, the reaction mixture was concentrated in vacuo. The residue was treated with 2M aqueous NaOH solution and extracted with Et2O. The organic layer was dried (Na2SO4), and concentrated in vacuo to afford 3-bromobutyric acid tert-butyl ester (6.05 g), which was used as such.

Workup

  1. customThe required 3-bromobutyric acid tert-butyl ester was prepared
  2. concentrationSubsequently, the reaction mixture was concentrated in vacuo
  3. additionThe residue was treated with 2M aqueous NaOH solution
  4. extractionextracted with Et2O
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f34bebdf5cb848be8bb0e4189ef93676
Source dataset
uspto-grants-2015_06
Patent number
US09045441B2

Reaction notes

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