N-bromobutanimide → 3-Bromo-6-fluoro-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole

HRID 1774086ノート

反応式

HRID 1774086 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C1C(=O)N([Br:29])C(=O)C1>C(Cl)(Cl)Cl>[Br:29][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH3:21])[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([F:1])=[CH:3][CH:4]=3

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 867279583-fluoro-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole

生成物 1

HCID 867279573-Bromo-6-fluoro-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole収率 84%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a solution of 3-fluoro-9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole (1.06 g, 3.71 mmol) in chloroform (20 ml) was added NBS (0.66 g, 3.71 mmol) batch-wise in an ice-water bath. After complete addition, the reaction mixture was allowed to warm to room temperature slowly and stirred overnight. The reaction mixture was washed with water and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure to give compound 6 in 84% yield. 1H NMR (400 MHz, CDCl3) δ 8.09-8.06 (m, 1H), 7.63-7.60 (m, 1H), 7.52-7.50 (m, 1H), 7.36-7.26 (m, 2H), 7.21-7.16 (m, 1H), 4.40 (d, J=5.6 Hz, 2H), 3.82-3.80 (m, 2H), 3.49-3.46 (m, 2H), 3.40-3.38 (m, 2H), 3.29 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 158.7, 156.3, 140.1, 137.4, 128.9, 124.2, 124.2, 123.2, 122.3, 122.2, 114.4, 114.1, 111.8, 110.8, 110.0, 109.9, 106.2, 106.0. HRMS (MALDI-TOF) m/z Calcd for C17H17BrFNO2 366.0499 Found 366.0502[M]+.

後処理

  1. additionAfter complete addition
  2. washThe reaction mixture was washed with water and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-7243bf41e24e40f596bdf3548d8d1c78
出典データセット
uspto-grants-2016_02
特許番号
US09255933B2

反応ノート

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