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

HRID 68645

반응식

HRID 68645 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7d5896dd4e01455cb6d9d5d82932a3be
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822459B2

연결된 노트

불러오는 중…