Hydrochloric Acid → Tert-butyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoate

HRID 888358노트

반응식

HRID 888358 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH:15]=[O:16])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C[Si](C)(C)[C:19]([F:22])([F:21])[F:20].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1.COC(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH:15]([OH:16])[C:19]([F:22])([F:21])[F:20])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 58095966Tert-butyl 3-bromo-5-formylbenzoate

생성물 1

HCID 59539580Tert-butyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 15413tert-Butyl methyl ether용매

실험 절차

To a solution of tert-butyl 3-bromo-5-formylbenzoate (Merck patent case No. 22407 PV; 5.7 g, 20.0 mmol) in THF (133 mL) at 0° C. were added trimethyl(trifluoromethyl)silane (4.44 mL, 30.0 mmol) and activated 4 Å molecular sieves. Tetrabutylammonium fluoride (1.0 M in THF; 6.0 mL, 6.0 mmol) was added dropwise. The reaction mixture was warmed to ambient temperature. After 3 h, aqueous 1N HCl (25 mL) and tert-butyl methyl ether (100 mL) were added. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and concentrated.

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8ed5e20ab1164ef28113adb3aa246377
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247401B2

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