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

HRID 335050

反応式

HRID 335050 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a51ff0d38edf42aba92bee747b035f5f
出典データセット
uspto-grants-2014_11
特許番号
US08883850B2

関連ノート

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