1,3-Dibromopropane → 1,2-Bis(4-(3-bromopropoxy)phenyl)ethane-1,2-dione

HRID 1620358

반응식

HRID 1620358 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][CH2:27][CH2:28][Br:29]>CN(C)C=O>[Br:29][CH2:28][CH2:27][CH2:26][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:18])[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:26][CH2:27][CH2:28][Br:29])=[CH:13][CH:12]=2)=[O:10])=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 4582044,4'-Dihydroxybenzil2회

생성물 1

HCID 682409451,2-Bis(4-(3-bromopropoxy)phenyl)ethane-1,2-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

1,2-bis(4-hydroxyphenyl)ethane-1,2-dione (2.6 g, 10.74 mmol) was dissolved in DMF and K2CO3 (5.9 g, 42.7 mmol) was added, 100 mmol of 1,3-dibromopropane and a catalytic amount of KI were then added. The mixture was heated to 80° C. and stirred for 3 days. TLC check showed 1,2-bis(4-hydroxyphenyl)ethane-1,2-dione disappeared. Dimethylformamide (DMF) was removed, and water was added, extracted by EtOAc, washed with brine, dried over MgSO4. The solvent was removed and the residue was purified by column chromatography to give 1,2-bis(4-(3-bromopropoxy)phenyl)ethane-1,2-dione 6 as a pale yellow solid, as confirmed by the following nuclear magnetic resonance (NMR) data obtained therefrom: 1H NMR (500 MHz, CDCl3): δ 7.94 (d, J=8.8 MHz, 4H), 6.99 (d, J=8.8 MHz, 4H), 4.20 (t, J=6.2 MHz, 4H), 3.61 (t, J=6.2 MHz, 4H), 2.34 (m, 4H) ppm.

후처리

  1. customDimethylformamide (DMF) was removed
  2. additionwater was added
  3. extractionextracted by EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed
  7. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-a631abe5a25c43389fdf3ed5a2ed2be3
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772443B2

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