2,2'-Bipyridine → Methyl 3-t-butyl-4-hydroxy-5-methylsulfanylbenzoate

HRID 385101ノート

反応式

HRID 385101 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13](I)[C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1C1C=CC=CN=1.[CH3:29][S:30]SC>CN(C)C=O.[Zn].[Ni](Br)Br>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([S:30][CH3:29])[C:14]=1[OH:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2]

参加物

7

反応物 3

HCID 14742,2'-BipyridineHCID 12232Dimethyl DisulfideHCID 12084815Methyl 3-t-butyl-4-hydroxy-5-iodobenzoate

生成物 1

HCID 86668170Methyl 3-t-butyl-4-hydroxy-5-methylsulfanylbenzoate収率 99.6%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 278492Nickel(II) bromide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

Methyl 3-t-butyl-4-hydroxy-5-iodobenzoate (1.00 g) was dissolved in N,N-dimethylformamide (10 mL), and 2,2′-bipyridine (47 mg), zinc powder (391 mg), nickel bromide (66 mg) and dimethyl disulfide (142 mg) were added to the solution, and then the mixture was stirred at 130° C. for 1 hour. After the reaction solution was filtered, 1N hydrochloric acid was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=12:1) to obtain the title compound (382 mg) as a pale yellow oily substance.

後処理

  1. filtrationAfter the reaction solution was filtered
  2. addition1N hydrochloric acid was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=12:1)

出典と根拠

ORDレコード
ord-0130ce09b54c4c719501736648c1348e
出典データセット
uspto-grants-2013_02
特許番号
US08367843B2

反応ノート

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