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

HRID 402827

Reaction equation

[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]

Participants

Conditions

Temperature: 0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-719259b39ba4474b81d51115e00d21d3
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742110B2

Linked notes

Loading…