Potassium Carbonate → tert-butyl N-(4-chloro-5-methyl-2-nitrophenyl)carbamate

HRID 498170ノート

反応式

HRID 498170 の反応式
[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[C:12](Cl)[C:11]([Cl:15])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])([CH3:4])([CH3:3])[CH3:2].[C:20](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.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>[C:1]([O:5][C:6](=[O:19])[NH:7][C:8]1[CH:13]=[C:12]([CH3:20])[C:11]([Cl:15])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 69489445tert-butyl N-(4,5-dichloro-2-nitrophenyl)carbamate

生成物 1

HCID 69489578tert-butyl N-(4-chloro-5-methyl-2-nitrophenyl)carbamate収率 48%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

To a suspension of (4,5-dichloro-2-nitro-phenyl)-carbamic acid tert.-butyl ester (Example A20) (10.0 g, 32.6 mmol), tetrakis(triphenylphosphine)palladium (3.76 g, 3.26 mmol) and potassium carbonate (13.5 g, 97.7 mmol) in dioxane/water (9:1; 100 ml) was added at RT trimethylboroxine (4.53 ml, 32.6 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 19:1) to yield a light yellow solid (4.45 g, 48%).

後処理

  1. filtrationfiltered
  2. customevaporated
  3. custompurified by column chromatography on silica gel (hexane/ethyl acetate 19:1)

出典と根拠

ORDレコード
ord-f49d5c4f06e14d1ba1719cbece00105c
出典データセット
uspto-grants-2005_09
特許番号
US06949542B2

反応ノート

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