1-Chloro-2,4-Dinitrobenzene → 2,4-Dinitro-1-(2-phenylchroman-6-yloxy)-benzene

HRID 31229

反応式

HRID 31229 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[O:17][CH:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][CH2:14]2)([O-:3])=[O:2].OC1C=C2C(=CC=1)OC(C1C=CC=CC=1)CC2.[OH-].[K+].[N+:46](C1C=C([N+]([O-])=O)C=CC=1Cl)([O-:48])=[O:47]>CS(C)=O>[N+:1]([C:4]1[CH:9]=[C:8]([N+:46]([O-:48])=[O:47])[CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[O:17][CH:16]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:15][CH2:14]2)([O-:3])=[O:2]

参加物

6

反応物 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 14797Potassium HydroxideHCID 179784752-Nitro-1-(2-phenylchroman-6-yloxy)-benzeneHCID 212875382-Phenylchroman-6-ol

生成物 1

HCID 179785452,4-Dinitro-1-(2-phenylchroman-6-yloxy)-benzene

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

2,4-Dinitro-1-(2-phenylchroman-6-yloxy)-benzene was prepared as described for 2-nitro-1-(2-phenylchroman-6-yloxy)-benzene in Example 29(a) except that 6-hydroxyflavane (0.226 g) was used in 5 ml of dry DMSO under nitrogen. Also KI (0.249 g) and KOH (0.112g) and 2,4-dinitrochlorobenzene (0.210 mg) were added in similar manner. Product was purified by column chromatography (CH2Cl2:n-heptane/75:25 as the eluant). 1H-NMR (400 MHz; d6-DMSO): δ 8.88 (d, 1H, J=2.8 Hz), 8.45 (dd, 1H, J=9.4 Hz, J=2.9 Hz), 7.48-7.30 (m, 5H), 7.14 (d, 1H, J=9.3 Hz), 7.10 (d, 1H, J=2.8 Hz), 7.05 (dd, 1H, J=8.8 Hz, J=2.9 Hz), 6.98 (d, 1H, J=8.7 Hz), 5.16 (dd, 1H, J=10.2 Hz, J=2.1 Hz), 3.08-2.93 (m, 1H), 2.83-2.71 (m, 1H), 2.25-2.13 (m, 1H), 2.08-1.94 (m, 1H).

後処理

  1. customProduct was purified by column chromatography (CH2Cl2

出典と根拠

ORDレコード
ord-561a39b5060f4dc4a20e7791a577f847
出典データセット
uspto-grants-2008_09
特許番号
US07425568B2

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