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

HRID 521429ノート

反応式

HRID 521429 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-51a51f0a75d34437838c9354421e3d6e
出典データセット
uspto-grants-2016_05
特許番号
US09328071B2

反応ノート

読み込み中…