1-Bromo-4-fluorobenzene → HCID 18679488、化合物

HRID 1633656ノート

反応式

HRID 1633656 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2.[Br:12][C:13]1[CH:18]=[CH:17][C:16](F)=[CH:15][CH:14]=1.C1OCCOCCOCCOCCOCCOC1.[F-].[K+]>CS(C)=O.O.CCOCC>[Br:12][C:13]1[CH:18]=[CH:17][C:16]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[CH:6]=[CH:7]2)=[CH:15][CH:14]=1

参加物

8

反応物 4

HCID 99931-Bromo-4-fluorobenzene2 回HCID 138725-MethoxyindoleHCID 2855718-Crown-62 回HCID 522689Potassium Fluoride2 回

生成物 1

HCID 18679488HCID 18679488、化合物収率 84.4%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
120 °C

実験手順

To 14.7 g (0.1 mol) 5-methoxyindole in 100 ml DMSO were added 32.6 ml (0.3 mol) 1-bromo-4-fluorobenzene, 1.06 g (0.04 mol) 18-crown-6 and 10.92 g (60 mmol) KF on alox. The suspension was heated to 120° C. for 48 h. Additional 21.7 ml (0.2 mol) 1-bromo-4-fluorobenzene, 1.06 g (0.04 mol) 18-crown-6 and 10.92 g (60 mmol) KF on alox were added, and the mixture was stirred at 130° C. for 20 h. At RT, ether and water were added, the phases were separated and the inorganic phase was extracted with ether. The combined organic phases were washed with water and dried over Na2SO4. The residue was triturated in ethanol to yield 25.5 g (84%) 1-(4-Bromo-phenyl)-5-methoxy-1H-indole as light brown solid, mp 90-91° C., MS: 301 (M, 1Br).

後処理

  1. customthe phases were separated
  2. extractionthe inorganic phase was extracted with ether
  3. washThe combined organic phases were washed with water
  4. dry with materialdried over Na2SO4
  5. customThe residue was triturated in ethanol

出典と根拠

ORDレコード
ord-e4d9d1087d064b708d22f16a3a218aa3
出典データセット
uspto-grants-2003_01
特許番号
US06503907B2

反応ノート

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