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

HRID 1617294

반응식

HRID 1617294 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 10129912Zinc(II) fluoride촉매HCID 178418851HCID 178418851, 화합물촉매HCID 962Water용매

반응 조건

온도
70 °C

실험 절차

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)

후처리

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

출처 및 근거

ORD 기록
ord-9742f662022441e5bf377bc95ae683c2
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765957B2

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