4-Iodophenol → 2-(2-(4-Iodophenoxy)ethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene

HRID 710351노트

반응식

HRID 710351 반응식
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][C:12]1[CH:13]2[CH2:18][CH:15]([CH2:16][CH:17]=1)[C:14]2([CH3:20])[CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][C:12]2[CH:13]3[CH2:18][CH:15]([CH2:16][CH:17]=2)[C:14]3([CH3:19])[CH3:20])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 202771482-(2-Bromoethyl)-6,6-dimethylbicyclo(3.1.1)hept-2-ene2회

생성물 1

HCID 667267162-(2-(4-Iodophenoxy)ethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene수율 28.2%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 4-iodophenol (0.4 g; 1.82 mmol), 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene (0.45 g, 1.97 mmol) and K2CO3 (0.3 g, 2.17 mmol) in anhydrous DMF (5 ml) was stirred overnight at room temperature. Another portion of 2-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]hept-2-ene (0.3 g) was added and stirring was continued for 6 h. The mixture was diluted to 50 ml with EtOAc and washed with H2O (50 ml). The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2) to give the title product (0.189 g; 28%), as pale paste. 1H-NMR (CDCl3) 0.81 (s, 3H); 1.26 (s, 3H); 2.06-2.44 (m, 8H); 3.91 (tr, 2H, J=6.97 Hz); 5.32 (s, 1H); 6.64 (d, 2H, J=8.96 Hz); 7.51 (d, 2H, J=8.96 Hz).

후처리

  1. stirringstirring
  2. waitwas continued for 6 h
  3. washwashed with H2O (50 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customthe residue was purified by FCC (SiO2)

출처 및 근거

ORD 기록
ord-98d837e8d00a431dbda479b6a2edd2d8
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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