1-Bromo-3-(trifluoromethoxy)benzene → Ethyl 4-[3-(trifluoromethoxy)phenyl]butanoate

HRID 63088ノート

反応式

HRID 63088 の反応式
[Br-].[CH2:2]([O:4][C:5](=[O:10])[CH2:6][CH2:7][CH2:8][Zn+])[CH3:3].Br[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=1>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:20][C:19]([F:21])([F:22])[O:18][C:14]1[CH:13]=[C:12]([CH2:8][CH2:7][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:10])[CH:17]=[CH:16][CH:15]=1

参加物

5

反応物 2

HCID 5199641-Bromo-3-(trifluoromethoxy)benzeneHCID 178471550HCID 178471550、化合物

生成物 1

HCID 86728216Ethyl 4-[3-(trifluoromethoxy)phenyl]butanoate収率 41%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

4-Ethoxy-4-oxobutylzinc bromide solution (25 mL, 0.5 M in THF, 12.5 mmol) was added to a solution of 1-bromo-3-(trifluoromethoxy)benzene (2.6 g, 10.8 mmol) in THF (10 mL) under N2. Pd(dppf)Cl2 (1.18 g, 1.62 mmol) was added, and the reaction was heated at reflux for 3 h. The solution was concentrated and purified by silica gel chromatography (0-20% EtOAc/hexanes) to give 1.22 g (41%) of the title compound as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ 1.26 (3H, t, J=7.2 Hz), 1.91-2.00 (2H, m), 2.32 (2H, t, J=7.4 Hz), 2.67 (2H, t, J=7.4 Hz), 4.13 (2H, q, J=7.2 Hz), 7.03-7.07 (2H, m), 7.11 (1H, d, J=7.7 Hz), 7.30 (1H, t, J=7.7 Hz).

後処理

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 3 h
  3. concentrationThe solution was concentrated
  4. custompurified by silica gel chromatography (0-20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-44e37a97fb44476fbf5e4ea2d412b24a
出典データセット
uspto-grants-2016_09
特許番号
US09447045B2

反応ノート

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