Dichloromethane → 2-Nitro-1-(2-phenylchroman-6-yloxy)-benzene

HRID 31225

反応式

HRID 31225 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH2:5]2.[OH-].[K+].Cl[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28].C(Cl)Cl>CS(C)=O>[N+:27]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][CH2:5]2)([O-:29])=[O:28]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 69451-Chloro-2-nitrobenzeneHCID 14797Potassium HydroxideHCID 212875382-Phenylchroman-6-ol

生成物 1

HCID 179784752-Nitro-1-(2-phenylchroman-6-yloxy)-benzene

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

6-Hydroxyflavane (0.150 g) was dissolved in dry DMSO (5 ml) under nitrogen. KI (0.166 g) and KOH (0.074g) were added and solution was stirred at room temperature for 15 minutes. 2-Chloro-1-nitrobenzene (0.104 g) was added and the solution was stirred at +90° C. for 2.5 hours. Cooled solution was taken up with CH2Cl2 and washed with H2O and 2M NaOH. Phases were separated and water phase was washed CH2Cl2. All organic phases were combined and washed with 1M HCl and then H2O (until pH˜7) and brine. Solution was dried over Na2SO4 and purified with filtration through the small silica column in CH2Cl2:n-heptane (60:40). 1H-NMR (300 MHz; d6-DMSO): δ 8.01 (dd, 1H, J=8.1 Hz; J=1.7 Hz), 7.69 (m, 1H), 7.50-7.31 (m, 5H), 7.31-7.24 (m, 1H), 7.04 (dd, 1H, J=8.5 Hz; J=1.2 Hz), 6.92 (s, 1H), 6.90 (s, 2H), 5.12 (dd, 1H, J=10.1 Hz; J=2.3 Hz), 2.95 (ddd, 1H, J=16.9 Hz; J=11.2 Hz, J=5.8 Hz), 2.73 (ddd, 1H, J=16.9 Hz; J=3.2 Hz, J=1.7 Hz), 2.25-2.10 (m, 1H), 2.08-1.90 (m, 1H).

後処理

  1. stirringthe solution was stirred at +90° C. for 2.5 hours
  2. washwashed with H2O and 2M NaOH
  3. customPhases were separated
  4. washwater phase was washed CH2Cl2
  5. washwashed with 1M HCl
  6. dry with materialSolution was dried over Na2SO4
  7. filtrationpurified with filtration through the small silica column in CH2Cl2:n-heptane (60:40)

出典と根拠

ORDレコード
ord-d43da5d2175a43c7bb5ecbd4fc202682
出典データセット
uspto-grants-2008_09
特許番号
US07425568B2

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