Water → Ethyl 2-(3-bromo-5-chloro-4-(2,2,2-trifluoroethoxy)phenyl)-4-methylpentanoate

HRID 385333ノート

反応式

HRID 385333 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([Cl:9])[C:7]=1[OH:8].C([O-])([O-])=O.[K+].[K+].[F:26][C:27]([F:31])([F:30])[CH2:28]I.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]([CH2:16][CH:17]([CH3:18])[CH3:19])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]([Cl:9])[C:7]=1[O:8][CH2:28][C:27]([F:31])([F:30])[F:26]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 677091,1,1-Trifluoro-2-iodoethaneHCID 57995536Ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)-4-methylpentanoate

生成物 1

HCID 57995655Ethyl 2-(3-bromo-5-chloro-4-(2,2,2-trifluoroethoxy)phenyl)-4-methylpentanoate収率 569%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of ethyl 2-(3-bromo-5-chloro-4-hydroxyphenyl)-4-methylpentanoate (2 g, 0.57 mmol) and K2CO3 (1.58 g, 0.011 mol) in dry DMF (20 mL), slowly added trifluoroethyl iodide (7.2 g, 3.39 ml, 0.034 mol) at room temperature. Upon completion of the addition, the reaction mixture was slowly heated to 100° C. for 4 h. Upon completion, the reaction mixture was poured into water and extracted with ethyl acetate (2×50 mL). The combined organic layer were washed with water, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography over silica gel (hexane/EtOAc) to give ethyl 2-(3-bromo-5-chloro-4-(2,2,2-trifluoroethoxy)phenyl)-4-methylpentanoate (1.4 g, 60% yield). 1HNMR (CDCl3, 400 MHz): 7.43 (s, 1H); 7.34 (s, 1H); 4.4 (q, 2H), 4.13 (q, 2H); 3.55 (t, 1H); 1.93 (m, 1H), 1.58 (m, 1H); 1.45 (m, 1H); 1.24 (t, 3H), 0.92 (d, 6H);

後処理

  1. customat room temperature
  2. additionUpon completion of the addition
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layer were washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash column chromatography over silica gel (hexane/EtOAc)

出典と根拠

ORDレコード
ord-20c485bb9c464c12a7ac363cc581d7db
出典データセット
uspto-grants-2013_02
特許番号
US08367863B2

反応ノート

読み込み中…