Toluene → 1-(3-Bromophenyl)-3-(4-fluorophenoxy)azetidine

HRID 522931ノート

反応式

HRID 522931 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[F:9][C:10]1[CH:20]=[CH:19][C:13]([O:14][CH:15]2[CH2:18][NH:17][CH2:16]2)=[CH:12][CH:11]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:8][C:4]1[CH:3]=[C:2]([N:17]2[CH2:18][CH:15]([O:14][C:13]3[CH:12]=[CH:11][C:10]([F:9])=[CH:20][CH:19]=3)[CH2:16]2)[CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 5

HCID 1140TolueneHCID 79271,3-DibromobenzeneHCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 214287303-(4-Fluorophenoxy)azetidine

生成物 1

HCID 673548151-(3-Bromophenyl)-3-(4-fluorophenoxy)azetidine収率 30%

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
100 °C

実験手順

To a solution of 1, 3-dibromobenzene (500 mg, 2.13 mmol) and 3-(4-fluorophenoxy)azetidine (357 mg, 2.13 mmol) in toluene (7 mL, 3 mmol) was added cesium carbonate (600 mg, 5.3 mmol) and degassed for 15 min. Pd2(dba)3 (97 mg, 0.106 mmol) and BINAP (66 mg, 0.106 mmol) were added and the mixture was heated in the microwave for 30 min at 100° C. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc (2×30 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography provided 1-(3-bromophenyl)-3-(4-fluorophenoxy)azetidine (200 mg, 30%) as a solid. Observed mass (M+1): 322.1.

後処理

  1. customdegassed for 15 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. extractionextracted with EtOAc (2×30 mL)
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel column chromatography

出典と根拠

ORDレコード
ord-8885093045b5433bb7d6a5a19411150c
出典データセット
uspto-grants-2016_05
特許番号
US09334269B2

反応ノート

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