Methyl iodide → Methyl 2-(3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate

HRID 1930139노트

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HRID 1930139 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[Cl:11][C:12]1[CH:13]=[C:14]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH:15]=[CH:16][C:17]=1[B:18]1[O:22][C:21]([CH3:24])([CH3:23])[C:20]([CH3:26])([CH3:25])[O:19]1.[CH3:32]I.[Cl-].[NH4+]>C1COCC1.O.C(OCC)(=O)C>[Cl:11][C:12]1[CH:13]=[C:14]([CH:27]([CH3:32])[C:28]([O:30][CH3:31])=[O:29])[CH:15]=[CH:16][C:17]=1[B:18]1[O:22][C:21]([CH3:23])([CH3:24])[C:20]([CH3:25])([CH3:26])[O:19]1

참가 물질

8

반응물 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2733832Lithium HexamethyldisilazideHCID 58464478Benzeneacetic acid, 3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester2회

생성물 1

HCID 59627648Methyl 2-(3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate수율 56.1%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

Lithium bis(trimethylsilyl)amide (7.79 mL, 7.79 mmol) was added to methyl 2-(3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate (Intermediate 2-7; 2.2 g, 7.08 mmol) in THF (50 mL) cooled to 0° C. under nitrogen. The resulting solution was stirred at 0° C. for 30 minutes. Next methyl iodide (0.530 mL, 8.50 mmol) was added and the reaction stirred for 30 minutes Ammonium chloride (satd) (50 mL) was added with vigorous stirring, ethyl acetate (100 mL) and water (50 mL) were added and the organic phase separated, washed with water (50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 40% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford methyl 2-(3-chloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate (1.290 g, 56.1%) as a colourless oil.

후처리

  1. additionwere added
  2. customthe organic phase separated
  3. washwashed with water (50 mL) and saturated brine (50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto afford crude product
  8. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 40% EtOAc in isohexane
  9. customPure fractions were evaporated to dryness

출처 및 근거

ORD 기록
ord-dd314a89ba3d4660bbbbdcedff6c372b
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188092B2

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