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

HRID 1050703
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HRID 1050703 반응식
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]
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8

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-512fe2700cd9425fbc628b0747544a2d
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09382424B2

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