Methyl 3-bromo-5-formylbenzoate → Methyl 3-bromo-5-vinylbenzoate

HRID 1845308ノート

反応式

HRID 1845308 の反応式
[CH2:1]([Li])CCC.[Br:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([CH:17]=O)[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:6][C:7]1[CH:8]=[C:9]([CH:14]=[C:15]([CH:17]=[CH2:1])[CH:16]=1)[C:10]([O:12][CH3:13])=[O:11]

参加物

5

反応物 2

HCID 11436457Methyl 3-bromo-5-formylbenzoateHCID 178418339Butyllithium

生成物 1

HCID 58188041Methyl 3-bromo-5-vinylbenzoate

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
0 °C

実験手順

To a stirred solution of methyltriphenylphosphonium bromide (350 mg, 0.97 mmol) in THF (3 mL) at −78° C. under nitrogen was added dropwise 2.5 M of n-butyllithium in tetrahydrofuran (0.31 mL, 0.78 mmol). The mixture was gradually warmed until a yellow color persisted. The mixture was cooled to 0° C. and a solution of methyl 3-bromo-5-formylbenzoate (157 mg, 0.65 mmol) in THF (2 mL) was added dropwise. After being stirred for 20 min at 0° C., the mixture was quenched with saturated aq. NH4Cl and extracted with EtOAc. The organic layer was separated and washed with brine, dried, and concentrated. The residue was purified by flash column to afford the title compound.

後処理

  1. temperatureThe mixture was gradually warmed until a yellow color
  2. customthe mixture was quenched with saturated aq. NH4Cl
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified by flash column

出典と根拠

ORDレコード
ord-86c45a0e9602481894e034d3a0e12f67
出典データセット
uspto-grants-2015_02
特許番号
US08946439B2

反応ノート

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