Water → Methyl 4-[(5-bromopentyl)thio]benzoate

HRID 68645

反応式

HRID 68645 の反応式
[SH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][S:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1

参加物

6

反応物 4

HCID 962WaterHCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 237573Methyl 4-sulfanylbenzoate

生成物 1

HCID 67164237Methyl 4-[(5-bromopentyl)thio]benzoate収率 73.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of methyl 4-mercaptobenzoate (3.39 g) and 1,5-dibromopentane (9.31 g) in dimethyl formamide (100 mL), potassium carbonate (3.07 g) was added. The reaction mixture was stirred at room temperature for 3 hours. To the reaction mixture, water (300 mL) was added and the aqueous layer was extracted twice with an n-hexane-ethyl acetate solution (n-hexane:ethyl acetate=1:1) (150 mL). The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0→8:2) to obtain the title compound (4.69 g) having the following physical properties.

後処理

  1. extractionthe aqueous layer was extracted twice with an n-hexane-ethyl acetate solution (n-hexane:ethyl acetate=1:1) (150 mL)
  2. washThe combined organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0→8:2)

出典と根拠

ORDレコード
ord-7d5896dd4e01455cb6d9d5d82932a3be
出典データセット
uspto-grants-2014_09
特許番号
US08822459B2

関連ノート

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