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

HRID 1771735ノート

反応式

HRID 1771735 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-673ef78312ad46849abe535ceff81b24
出典データセット
uspto-grants-2016_02
特許番号
US09249085B2

反応ノート

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