1-Bromopropane → 1-Iodo-4-propoxybenzene

HRID 625889노트

반응식

HRID 625889 반응식
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH3:12].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 78401-BromopropaneHCID 10340Sodium CarbonateHCID 108944-Iodophenol

생성물 1

HCID 132969221-Iodo-4-propoxybenzene수율 87%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A suspension of 4-iodophenol (3 g, 13.64 mmol), 1-bromopropane (1.845 g, 15.00 mmol), and sodium carbonate (7.54 g, 54.5 mmol) in DMF (30 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was diluted with water (250 mL) and extracted with EtOAc (3×75 mL). The combined organic extracts were washed with 0.5M NaOH (2×50 mL), and water (2×50 mL), and then dried over MgSO4. The solvent was removed. The crude product (3.11 g) was obtained, which was directly used for the next reaction without further purification. 1H NMR (400 MHz, chloroform-d) δ 7.61-7.53 (m, 2H), 6.74-6.67 (m, 2H), 3.90 (t, J=6.5 Hz, 2H), 1.88-1.76 (m, 2H), 1.05 (t, J=7.4 Hz, 3H).

후처리

  1. extractionextracted with EtOAc (3×75 mL)
  2. washThe combined organic extracts were washed with 0.5M NaOH (2×50 mL), and water (2×50 mL)
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed

출처 및 근거

ORD 기록
ord-366ce2d833d5422c8c97f48f5b992598
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09308236B2

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