Trimethylboroxine → (5-Methyl-2-nitro-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester

HRID 1266728노트

반응식

HRID 1266728 반응식
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[C:12](Cl)[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[N+:19]([O-:21])=[O:20])([CH3:4])([CH3:3])[CH3:2].[CH3:23]B1OB(C)OB(C)O1>O1CCOCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:13]=[C:12]([CH3:23])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:10][C:9]=1[N+:19]([O-:21])=[O:20])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 2

HCID 574072TrimethylboroxineHCID 69489376(5-Chloro-2-nitro-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester

생성물 1

HCID 69486745(5-Methyl-2-nitro-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester수율 69%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

To a suspension of (5-chloro-2-nitro-4-trifluoromethyl-phenyl)-carbamic acid tert-butyl ester (Example A11) (5.00 g, 14.7 mmol) and tetrakis(triphenylphosphine)-palladium in dioxane/water (9:1; 50 ml) was added at RT trimethylboroxine (2.04 ml, 14.7 mmol). The reaction mixture was stirred under reflux conditions for 15 h, filtered, evaporated and purified by column chromatography on silica gel (hexane/ethyl acetate 9:1) to yield a light yellow solid (3.25 g, 69%).

후처리

  1. filtrationfiltered
  2. customevaporated
  3. custompurified by column chromatography on silica gel (hexane/ethyl acetate 9:1)

출처 및 근거

ORD 기록
ord-ee72be5f478a445d9b4fd0c13fdfacc0
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06548495B2

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