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

HRID 33029

反応式

HRID 33029 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2c763baf62ac4a7ab704f36e92b56a0b
出典データセット
uspto-grants-2008_09
特許番号
US07427613B2

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