tert-Butanol → Tert-butyl 3-bromobutanoate

HRID 2167903노트

반응식

HRID 2167903 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 57092335Tert-butyl 3-bromobutanoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f34bebdf5cb848be8bb0e4189ef93676
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045441B2

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