4-Bromophenol → 1-Bromo-4-(2,2,2-trifluoroethoxy)benzene

HRID 883631

반응식

HRID 883631 반응식
S(C1C=CC(C)=CC=1)(O[CH2:5][C:6]([F:9])([F:8])[F:7])(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH:23]1[C:28]([OH:29])=[CH:27][CH:26]=[C:25]([Br:30])[CH:24]=1>CN(C=O)C>[Br:30][C:25]1[CH:26]=[CH:27][C:28]([O:29][CH2:5][C:6]([F:9])([F:8])[F:7])=[CH:23][CH:24]=1

참가 물질

5

반응물 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)

생성물 1

HCID 229138831-Bromo-4-(2,2,2-trifluoroethoxy)benzene수율 54%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

To a stirred solution of trifluoroethyl tosylate (1.5 g, 5.8 mmol) in DMF (20 mL) was added K2CO3 (4 g, 29.4 mmol) followed by addition of p-bromo phenol (1.1 g, 6.46 mmol) at RT under inert atmosphere. The reaction mixture was stirred at 120° C. for 6 h. The volatiles were evaporated under reduced pressure; the residue was diluted with water (5 mL) and extracted with ethyl acetate (3×30 mL). The organic layer was washed with water, brine and dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude compound was purified by silica gel column chromatography eluting with 5% EtOAc/hexane to afford the desired product (0.8 g, 3.13 mmol, 53.3%) as semi solid. 1H NMR (200 MHz, CDCl3): □ 7.44-7.38 (m, 2H), 6.86-6.80 (m, 2H), 4.38-4.25 (m, 2H).

후처리

  1. customThe volatiles were evaporated under reduced pressure
  2. additionthe residue was diluted with water (5 mL)
  3. extractionextracted with ethyl acetate (3×30 mL)
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude compound was purified by silica gel column chromatography
  9. washeluting with 5% EtOAc/hexane

출처 및 근거

ORD 기록
ord-260b662328784621993316d06e5aabb8
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236962B2

연결된 노트

불러오는 중…