Dichloromethane → Ethyl 5-(bromomethyl)-2-(trifluoromethyl)furan-3-carboxylate

HRID 237249ノート

反応式

HRID 237249 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[O:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=[O:5])[CH3:2].[Br:16]N1C(=O)CCC1=O.C(Cl)Cl.C([O-])(O)=O.[Na+]>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][Br:16])[O:8][C:7]=1[C:12]([F:15])([F:13])[F:14])=[O:5])[CH3:2]

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 2737208Ethyl 5-methyl-2-(trifluoromethyl)furan-3-carboxylate

生成物 1

HCID 13237850Ethyl 5-(bromomethyl)-2-(trifluoromethyl)furan-3-carboxylate収率 38%

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

To a solution of 5-methyl-2-trifluoromethyl-furan-3-carboxylic acid ethyl ester (0.95 g, 4.5 mmol) in CCl4 (12 mL) was added N-bromosuccinimide (0.84 g, 4.8 mmol) followed by AIBN (0.004 g, 0.01 mmol). After refluxing for 2 h, analytical HPLC analysis confirmed the reaction was complete. The reaction was cooled to rt, then CH2Cl2 and sat'd NaHCO3 (aq.) were added. The organic portion was separated and dried to provide the crude residue as a yellow oil. This material was purified by RP HPLC to provide the title compound (510 mg, 38%). MS (ESI): mass calcd. for C9H8BrF3O3, 300.0; m/z found, 302.9 [M+H]+. 1H NMR (CDCl3): 6.84 (s, 1H), 4.44 (s, 2H), 4.34 (q, J=7.2 Hz, 2H), 1.36 (t, J=7.1 Hz, 3H).

後処理

  1. temperatureAfter refluxing for 2 h
  2. customThe organic portion was separated
  3. customdried
  4. customto provide the crude residue as a yellow oil
  5. customThis material was purified by RP HPLC

出典と根拠

ORDレコード
ord-50a405bed03c4c52a484f67738a091c4
出典データセット
uspto-grants-2014_02
特許番号
US08642583B2

反応ノート

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