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1-Butanol → 4,7-bis(4-isobutoxyphenyl)-2-isobutyl-2H-benzo[d][1,2,3]triazole

HRID 1050703
ノート
印刷プレビュー

反応式

HRID 1050703 の反応式
Br[C:2]1[C:10]2[C:6](=[N:7][N:8]([CH2:11][CH:12]([CH3:14])[CH3:13])[N:9]=2)[C:5](Br)=[CH:4][CH:3]=1.[CH2:16]([O:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)[CH:17]([CH3:19])[CH3:18].[C:30](=[O:33])([O-])[O-].[Na+].[Na+].[C:36]1(C)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.[CH2:43](O)[CH2:44][CH2:45]C>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:16]([O:20][C:21]1[CH:26]=[CH:25][C:24]([C:2]2[C:10]3[C:6](=[N:7][N:8]([CH2:11][CH:12]([CH3:14])[CH3:13])[N:9]=3)[C:5]([C:36]3[CH:37]=[CH:38][C:39]([O:33][CH2:30][CH:44]([CH3:45])[CH3:43])=[CH:40][CH:41]=3)=[CH:4][CH:3]=2)=[CH:23][CH:22]=1)[CH:17]([CH3:19])[CH3:18]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 2631-ButanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 162177734-Isobutoxyphenylboronic acidHCID 866799204,7-Dibromo-2-isobutyl-2H-benzo[d][1,2,3]triazole

生成物 1

HCID 866799194,7-bis(4-isobutoxyphenyl)-2-isobutyl-2H-benzo[d][1,2,3]triazole

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回

反応条件

温度
100 °C

実験手順

A mixture of Intermediate K (1.32 g, 4.0 mmol), 4-isobutoxyphenylboronic acid (1.94 g, 10.0 mmol), tetrakis(triphenylphosphine)palladium(0) (1.00 g, 0.86 mmol), solution of sodium carbonate (2.12 g, 20 mmol) in water (15 mL), butanol (50 mL), and toluene (30 mL) was vigorously stirred and heated under argon at 100° C. for 16 hours. The reaction mixture was poured into water (300 mL), stirred for 30 minutes and extracted with toluene/ethyl acetate/hexane (5:3:2, 500 mL). The volatiles were removed under reduced pressure, and the residue was chromatographed (silica gel, hexane/dichloromethane, 1:1). The separated product was recrystallized from ethanol to give pure 4,7-bis(4-isobutoxyphenyl)-2-isobutyl-2H-benzo[d][1,2,3]triazole, Compound 42 (1.57 g, 83% yield). 1H NMR (400 MHz, CDCl3): δ 7.99 (d, J=8.7 Hz, 4H, 4-i-BuOC6H4), 7.55 (s, 2H, benzotriazole), 7.04 (d, J=8.8 Hz, 4H, 4-i-BuOC6H4), 4.58 (d, J=7.3 Hz, 2H, i-Bu), 3.79 (d, J=6.6 Hz, 4H, 4-i-BuOC6H4), 2.59 (m, 1H, i-Bu), 2.13 (m, 2H, 4-i-BuOC6H4), 1.04 (d, J=6.6 Hz, 12H, 4-i-BuOC6H4), 1.00 (d, J=6.6 Hz, 6H, i-Bu). UV-vis spectrum (PVB): λmax=359 nm. Fluorimetry (PVB): λmax=434 nm.

後処理

  1. stirringstirred for 30 minutes
  2. extractionextracted with toluene/ethyl acetate/hexane (5:3:2, 500 mL)
  3. customThe volatiles were removed under reduced pressure
  4. customthe residue was chromatographed (silica gel, hexane/dichloromethane, 1:1)
  5. customThe separated product was recrystallized from ethanol

出典と根拠

ORDレコード
ord-512fe2700cd9425fbc628b0747544a2d
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09382424B2

反応ノート

読み込み中…

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