Triphenylphosphine → 4-Bromo-3-(2-m-tolyl-ethoxy)-benzoic acid methyl ester

HRID 521429노트

반응식

HRID 521429 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([OH:11])[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][C:33]1[CH:34]=[C:35]([CH2:39][CH2:40]O)[CH:36]=[CH:37][CH:38]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[C:6]([O:11][CH2:40][CH2:39][C:35]2[CH:34]=[C:33]([CH3:32])[CH:38]=[CH:37][CH:36]=2)[CH:5]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 746483-MethylbenzeneethanolHCID 5363146Diisopropyl azodicarboxylateHCID 6425184Methyl 4-Bromo-3-hydroxybenzoate

생성물 1

HCID 670765654-Bromo-3-(2-m-tolyl-ethoxy)-benzoic acid methyl ester수율 102.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-Bromo-3-hydroxy-benzoic acid methyl ester (1.00 g, 4.32 mmol) and triphenylphosphine (1.36 g, 5.19 mmol) were dissolved in THF. 2-(3-Methylphenyl)-ethanol (2-m-tolyl-ethanol) (0.707 g, 5.19 mmol) was added, the mixture was cooled in an ice bath, and DIAD (1.05 g, 5.19 mmol) was added slowly with stirring. The ice bath was removed and stirring continued overnight at room temperature. The volatiles were evaporated in vacuo, and the residue was purified by silica gel chromatography (HEP/EA gradient) to give 1.55 g of the title compound.

후처리

  1. temperaturethe mixture was cooled in an ice bath
  2. customThe ice bath was removed
  3. stirringstirring continued overnight at room temperature
  4. customThe volatiles were evaporated in vacuo
  5. customthe residue was purified by silica gel chromatography (HEP/EA gradient)

출처 및 근거

ORD 기록
ord-51a51f0a75d34437838c9354421e3d6e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328071B2

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