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

HRID 1845308노트

반응식

HRID 1845308 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

HCID 58188041Methyl 3-bromo-5-vinylbenzoate

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-86c45a0e9602481894e034d3a0e12f67
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946439B2

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