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

HRID 2384940ノート

反応式

HRID 2384940 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
70 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-fade022164b841bd8f73f8282fd72965
出典データセット
uspto-grants-2012_09
特許番号
US08263772B2

反応ノート

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