Dimethylformamide → Methyl 2-(5-tert-butyl-2-hydroxy-4-nitrophenyl)-2-methylpropanoate

HRID 1617294

反応式

HRID 1617294 の反応式
Br[C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[OH:15].[CH3:16]/[C:17](/[CH3:26])=[C:18](/[O:24][CH3:25])\[O:19][Si](C)(C)C.CN(C)C=O>O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C.[F-].[Zn+2].[F-]>[C:8]([C:6]1[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]([OH:15])=[C:2]([C:17]([CH3:26])([CH3:16])[C:18]([O:24][CH3:25])=[O:19])[CH:7]=1)([CH3:11])([CH3:10])[CH3:9]

参加物

7

反応物 3

HCID 6228DimethylformamideHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-HCID 595441452-Bromo-4-tert-butyl-5-nitro-phenol

生成物 1

HCID 59544161Methyl 2-(5-tert-butyl-2-hydroxy-4-nitrophenyl)-2-methylpropanoate

試薬・触媒・溶媒 3

HCID 10129912Zinc(II) fluoride触媒HCID 178418851HCID 178418851、化合物触媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

A mixture of 2-bromo-4-tert-butyl-5-nitrophenol (15.00 g, 54.72 mmol), bis(tri-tert-butylphospine)palladium(0) (1.422 g, 2.783 mmol), zinc fluoride (2.82 g, 27.27 mmol), methyl trimethylsilyl dimethylketene acetal (MTDA) (19.35 g, 111.0 mmol), and dimethylformamide (150 mL) was heated at 70° C. for 18 h. The mixture was cooled to room temperature and diluted with water. After stirring for one hour, the aqueous phase was extracted with MTBE. The organic layer was dried in vacuo to afford the crude product as a brown solid. Purification of the product was accomplished by trituration in n-heptane. 1H-NMR (400 MHZ, DMSO-d6) δ 10.38 (s, 1H); 7.37 (s, 1H); 6.79 (s, 1H); 3.54 (s, 3H); 1.45 (s, 6H); 1.32 (s, 9H)

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionthe aqueous phase was extracted with MTBE
  3. customThe organic layer was dried in vacuo

出典と根拠

ORDレコード
ord-9742f662022441e5bf377bc95ae683c2
出典データセット
uspto-grants-2014_07
特許番号
US08765957B2

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