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

HRID 2102924ノート

反応式

HRID 2102924 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 86607392tert-Butyl 2-fluoro-4-formylbenzoate収率 61%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8a0c2969f92b4ff8b3bf8bbf93c882f2
出典データセット
uspto-grants-2009_08
特許番号
US07576099B2

反応ノート

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