Aluminum(III) Chloride → Methyl 2-(2-bromo-5-(4-iodo-3-nitrobenzoyl)thiophen-3-yl)acetate

HRID 1952498ノート

反応式

HRID 1952498 の反応式
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9].[I:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][C:14]=1[N+:22]([O-:24])=[O:23].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[Br:1][C:2]1[S:3][C:4]([C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:13]([I:12])=[C:14]([N+:22]([O-:24])=[O:23])[CH:15]=2)=[CH:5][C:6]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9]

参加物

5

反応物 3

HCID 6451240Aluminum(III) ChlorideHCID 57116941Methyl 2-(2-bromothiophen-3-yl)acetateHCID 589329354-Iodo-3-nitrobenzoyl chloride

生成物 1

HCID 67496104Methyl 2-(2-bromo-5-(4-iodo-3-nitrobenzoyl)thiophen-3-yl)acetate収率 64.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of methyl (2-bromothiophen-3-yl)acetate (120 mg, 0.51 mmol) and 4-iodo-3-nitrobenzoyl chloride (150 mg, 0.48 mmol) in anhydrous CH2Cl2 (10 mL) was added AlCl3 (260 mg, 1.95 mmol) in four portions in 10-minute intervals at room temperature. The resulting mixture was stirred overnight. The reaction mixture was slowly poured onto 5 g of ice and allowed to warm to room temperature. The aqueous phase was extracted with CH2Cl2 (3×15 mL). The combined organic layer was dried over MgSO4, filtered, and then concentrated in vacuo. MPLC purification (Hex:EtOAc/5:1) of the residue gave 2 as a light yellow solid (158 mg, 61%). 1H NMR (400 MHz, CDCl3) δ 8.27 (d, J=2.0 Hz, 1H), 8.22 (d, J=8.0 Hz, 1H), 7.70 (dd, J=2.0, 8.2 Hz, 1H), 7.48 (s, 1H), 3.74 (s, 3H), and 3.68 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 183.8, 170.0, 153.2, 142.9, 141.9, 138.3, 136.5, 135.8, 133.1, 125.7, 124.5, 91.8, 52.6, and 35.0.

後処理

  1. extractionThe aqueous phase was extracted with CH2Cl2 (3×15 mL)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customMPLC purification (Hex:EtOAc/5:1) of the residue

出典と根拠

ORDレコード
ord-a2eec6889eb34bdaad7ba431b95053ef
出典データセット
uspto-grants-2013_03
特許番号
US08404728B2

反応ノート

読み込み中…