Dimethylformamide → tert-Butyl 2-fluoro-4-formylbenzoate

HRID 2102924노트

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HRID 2102924 반응식
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([F:15])[CH:3]=1.[Li]CCCC.CN([CH:24]=[O:25])C>C1COCC1>[F:15][C:4]1[CH:3]=[C:2]([CH:24]=[O:25])[CH:14]=[CH:13][C:5]=1[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 46738774tert-Butyl 4-bromo-2-fluorobenzoateHCID 178418339Butyllithium

생성물 1

HCID 86607392tert-Butyl 2-fluoro-4-formylbenzoate수율 61%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a stirred solution of tert-butyl 4-bromo-2-fluorobenzoate (1.5 g, 5.45 mmol) in THF (70 mL) at −100° C. under argon was carefully added BuLi (2.5 M in hexane, 2.3 mL, 5.75 mmol). The mixture was kept at −100° C. to −80° C. for 1 h and then DMF (1.0 mL) in THF (5 mL) was added. After 1 h, the mixture was warmed to 0° C. and quenched by adding sat. aq NH4Cl, and extracted with EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), and concentrated under vacuum. The residue was purified by column chromatography on silica gel using EtOAc/hexane (0-10%) as eluent to give the product (750 mg, 61%) as a white solid.

후처리

  1. customat −100° C.
  2. waitAfter 1 h
  3. customquenched
  4. additionby adding sat. aq NH4Cl
  5. extractionextracted with EtOAc
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated under vacuum
  10. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-8a0c2969f92b4ff8b3bf8bbf93c882f2
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576099B2

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