1-Bromo-4-fluorobenzene → Tert-butyl 3-(4-bromophenoxy)azetidine-1-carboxylate

HRID 2384940노트

반응식

HRID 2384940 반응식
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11](F)=[CH:10][CH:9]=1.[C:15]([O:19][C:20]([N:22]1[CH2:25][CH:24]([OH:26])[CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16]>C1COCC1>[C:15]([O:19][C:20]([N:22]1[CH2:25][CH:24]([O:26][C:11]2[CH:12]=[CH:13][C:8]([Br:7])=[CH:9][CH:10]=2)[CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

참가 물질

5

반응물 3

HCID 99931-Bromo-4-fluorobenzeneHCID 2756801Tert-butyl 3-hydroxyazetidine-1-carboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 68605010Tert-butyl 3-(4-bromophenoxy)azetidine-1-carboxylate수율 46.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
70 °C

실험 절차

Add dropwise potassium tert-butoxide in THF (34.6 mL, 34.6 mmol) to a solution of p-bromofluorobenzene (6.1 g, 34.6 mmol) in THF (144 mL) and 3-hydroxy-azetidine-1-carboxylic acid tert-butyl ester (5.0 g, 28.9 mmol) at RT. Heat the mixture at 70° C. overnight. Cool the mixture to RT, quench with water, dilute with Et2O, and wash once with saturated NH4Cl. Back extract the aqueous with Et2O, dry the combined organics over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatography, eluting with 25% EtOAc/hexane to give 4.4 g (46%) of the title compound. LC-MS/ES m/z (81Br) 274 [M−tertBu+H]+.

후처리

  1. temperatureCool the mixture to RT
  2. customquench with water
  3. additiondilute with Et2O
  4. washwash once with saturated NH4Cl
  5. extractionBack extract the aqueous with Et2O
  6. dry with materialdry the combined organics over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate
  9. customPurify the crude material by flash chromatography
  10. washeluting with 25% EtOAc/hexane

출처 및 근거

ORD 기록
ord-fade022164b841bd8f73f8282fd72965
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263772B2

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