Methanol → methyl 4-bromo-3-(hydroxymethyl)benzoate

HRID 404403

반응식

HRID 404403 반응식
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[C:12](OC)=[O:13].[H-].C([Al+]CC(C)C)C(C)C.CO>C1COCC1.CCCCCC>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH2:12][OH:13]

참가 물질

6

반응물 3

HCID 887MethanolHCID 2824912Dimethyl 4-bromoisophthalateHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 22574933methyl 4-bromo-3-(hydroxymethyl)benzoate수율 38%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-78 °C

실험 절차

To a −78° C. solution of dimethyl 4-bromoisophthalate (21.0 g, 77 mmol)(commercially available from Maybridge) in THF (100 mL) was slowly added diisobutylaluminum hydride (269 mL, 269 mol, 1.0 M solution in hexane, commercially available from Sigma-Aldrich, St. Louis, Mo., USA) over 20 minutes. After stirring at −78° C. for 3 hours, the resulting mixture was treated with MeOH. Organic solvents were removed under reduced pressure and the residue was redissolved in EtOAc and washed with 1.0 N HCl. After removal of organic solvents under reduced pressure, purification of the residue through silica gel chromatography with 0-35% EtOAc in hexanes as eluents afforded 132.1 (7.1 g, 38%).

후처리

  1. customTo a −78° C.
  2. customOrganic solvents were removed under reduced pressure
  3. dissolutionthe residue was redissolved in EtOAc
  4. washwashed with 1.0 N HCl
  5. customAfter removal of organic solvents
  6. customunder reduced pressure, purification of the residue through silica gel chromatography with 0-35% EtOAc in hexanes as eluents

출처 및 근거

ORD 기록
ord-5485a2fc3de7450da3fae4918c561883
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748462B2

연결된 노트

불러오는 중…