2-Chlorophenol → 3-(4-Bromophenyl)prop-1-yl 2-chlorophenyl ether

HRID 33029

반응식

HRID 33029 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1O.N(C(OC(C)C)=O)=NC(OC(C)C)=O.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1

참가 물질

6

반응물 4

HCID 72452-ChlorophenolHCID 13831TributylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 105606143-(4-Bromophenyl)propan-1-ol

생성물 1

HCID 674208273-(4-Bromophenyl)prop-1-yl 2-chlorophenyl ether

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a sol. of 3-(4-bromophenyl)propan-1-ol (Glover S. A., et al.; Tetrahearon, 1990, 46, 7247; 24.5 g, 0.114 mol) in toluene (600 mL) under nitrogen were added 2-chlorophenol (17.4 mL, 0.171 mmol), diisopropyl azodicarboxylate (33.1 mL, 0.171 mol) and tri-n-butylphosphine (42.2 mL, 0.171 mol). The sol. was heated to reflux and stirred under reflux overnight. The sol. was allowed to cool to rt and the solvents were removed under reduced pressure. The residue was diluted in EtOAc and washed with aq. 1M HCl (1×) and aq. 1M NaOH (2×). The org. extracts were dried over MgSO4, filtered and the solvents were removed under reduced pressure. Purification of the residue by FC (petroleum ether→Et2O/petroleum ether 1:99→1:19) led to the tide compound (15.1 g, 41%). Rf=0.70 (EtOAc/heptane 1:3).

후처리

  1. temperatureThe sol. was heated
  2. temperatureto reflux
  3. temperatureunder reflux overnight
  4. customthe solvents were removed under reduced pressure
  5. additionThe residue was diluted in EtOAc
  6. washwashed with aq. 1M HCl (1×) and aq. 1M NaOH (2×)
  7. dry with materialextracts were dried over MgSO4
  8. filtrationfiltered
  9. customthe solvents were removed under reduced pressure
  10. customPurification of the residue by FC (petroleum ether→Et2O/petroleum ether 1:99→1:19)

출처 및 근거

ORD 기록
ord-2c763baf62ac4a7ab704f36e92b56a0b
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07427613B2

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