Dimethyl Sulfate → Methyl 1-methoxy-4-bromo-2-naphthoate

HRID 335050

반응식

HRID 335050 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[C:4]([C:13]([OH:15])=O)[CH:3]=1.S([O:21][CH3:22])(OC)(=O)=O.[C:23](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH3:23])=[C:4]([C:13]([O:21][CH3:22])=[O:15])[CH:3]=1

참가 물질

5

반응물 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 2893934-Bromo-1-hydroxynaphthalene-2-carboxylic acid

생성물 1

HCID 12084039Methyl 1-methoxy-4-bromo-2-naphthoate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 4-bromo-1-hydroxy-2-naphthoic acid (see Example 1, 1.63 g, 6.10 mmol) in 35 mL of acetone was added dimethyl sulfate (1.75 mL, 18.3 mmol) and potassium carbonate (2.95 g, 21.4 mmol). The reaction was heated to reflux for 14 hours, cooled to room temperature, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-20% ethyl acetate in hexanes to provide methyl 4-bromo-1-methoxy-2-naphthoate that gave a proton NMR spectra consistent with theory.

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 14 hours
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via silica gel chromatography
  6. washeluting with 0-20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-a51ff0d38edf42aba92bee747b035f5f
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883850B2

연결된 노트

불러오는 중…