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

HRID 237249노트

반응식

HRID 237249 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-50a405bed03c4c52a484f67738a091c4
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642583B2

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