Methyl 4-(bromomethyl)benzoate → HCID 18510220, 화합물

HRID 1371014

반응식

HRID 1371014 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:11][Si](C)(C)C)[C:9]#N)=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.BrC[C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[CH3:35][O:34][C:32](=[O:33])[C:31]1[CH:36]=[CH:37][C:28]([CH2:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[O:11])=[CH:29][CH:30]=1

참가 물질

7

반응물 4

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 2724141Tetrabutylammonium FluorideHCID 2733832Lithium HexamethyldisilazideHCID 117155522-(4-Fluorophenyl)-2-[(trimethylsilyl)oxy]acetonitrile

생성물 1

HCID 18510220HCID 18510220, 화합물수율 65.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매4회

실험 절차

To 2-(4-fluorophenyl)-2-[(trimethylsilyl)oxy]acetonitrile (0.500 g, 2.24 mmol) in degassed THF (11 ml) at −78° C. was added LHMDS 1M in THF (2.4 ml). To the previous reaction mixture a solution of methyl 4-(bromomethyl)benzoate (0.513 g, 2.25 mmol) in THF (2 ml) was then added. After a period of 1 h at r.t., tetrabutylammonium fluoride solution 1 M in THF (2.23 ml) was added to the reaction mixture and stirred for 10 minutes. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography using hexane/ethyl acetate 30% giving 0.4 g of the title compound.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-8d0496ff676b429dbd0e273701dac41f
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06583126B2

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