4-Methylmorpholine → Methyl 3,5-dibromo-4-{[(phenylsulfanyl)carbonothioyl]oxy}benzoate

HRID 402827

반응식

HRID 402827 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].CN1CCOCC1.Cl[C:22]([S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[S:23]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[O:12][C:22]([S:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[S:23])[C:5]([O:7][CH3:8])=[O:6]

참가 물질

6

반응물 3

HCID 79724-MethylmorpholineHCID 592675Phenyl ChlorodithioformateHCID 726975Methyl 3,5-dibromo-4-hydroxybenzoate

생성물 1

HCID 77230874Methyl 3,5-dibromo-4-{[(phenylsulfanyl)carbonothioyl]oxy}benzoate수율 99.9%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

Methyl 3,5-dibromo-4-hydroxybenzoate (1000 mg, 3.23 mmol) was dissolved in THF (16 mL) and N-methylmorpholine (0.709 mL, 6.45 mmol) was added. The mixture was cooled to 0° C. and phenyl chlorodithioformate (0.549 mL, 3.87 mmol) was added. The mixture was warmed to room temperature and stirred overnight. The mixture was diluted with EtOAc and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified by silica gel chromatography (0-15% EtOAc/hexanes) to yield the title compound as a clear oil (1491 mg).

후처리

  1. temperatureThe mixture was warmed to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (0-15% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-719259b39ba4474b81d51115e00d21d3
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08742110B2

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