Imidazole → Benzene, 1,5-difluoro-2-methyl-4-[[tris(1-methylethyl)silyl]oxy]-

HRID 1771735노트

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HRID 1771735 반응식
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].N1C=CN=C1.[CH3:16][CH:17]([Si:19](Cl)([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[CH3:18].O>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([CH3:9])=[CH:4][C:3]=1[O:10][Si:19]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:18])[CH3:16]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 139400Triisopropylsilyl chlorideHCID 846489282,4-Difluoro-5-methylphenol

생성물 1

HCID 89443589Benzene, 1,5-difluoro-2-methyl-4-[[tris(1-methylethyl)silyl]oxy]-수율 80%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 2,4-difluoro-5-methylphenol (780 mg, 5.41 mmol, 1.0 eq) and imidazole (442 mg, 6.5 mmol, 1.2 eq) in DMF (10 mL) at 0° C. was added TIPSCl (1.15 g, 5.95 mmol, 1.1 eq) dropwise. After the addition, the reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was then poured into water and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give a crude residue, which was purified by column chromatography (petroleum ether: EtOAc, 100:1) to give the title compound as a colorless oil (1.2 g, 80%).

후처리

  1. additionAfter the addition
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a crude residue, which
  8. customwas purified by column chromatography (petroleum ether: EtOAc, 100:1)

출처 및 근거

ORD 기록
ord-673ef78312ad46849abe535ceff81b24
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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