Dimethyl Sulfoxide → HCID 22666363, compound

HRID 1007937Notes

Reaction equation

[F:1][C:2]1[C:11]([O:12][CH3:13])=[C:10](F)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:21]([O:23][CH:24]([O:27][CH2:28][CH3:29])[CH2:25]Br)[CH3:22].O.C[S:32](C)=O>C(OCC)(=O)C>[CH2:21]([O:23][CH:24]([O:27][CH2:28][CH3:29])[CH2:25][S:32][C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[C:11]=1[O:12][CH3:13])[CH3:22]

Participants

Conditions

Temperature: 60 °C

Procedure

In 59 mL of dimethyl sulfoxide is dissolved 11.8 g of methyl 2,4-difluoro-3-methoxybenzoate, to which are added 23.0 g of potassium carbonate and 9.33 g of sodium hydrogen sulfide n-hydrate (purity 70%). The mixture is stirred at 60° C. for 2 hours. Then, 25 mL of bromoacetaldehyde diethyl acetal is added at the same temperature as above, and stirred at that temperature for 3 hours. Water and ethyl acetate are added to the reaction mixture, and the organic layer is separated. The organic layer is washed with saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by column chromatography (eluent: hexane-ethyl acetate=5:1) to obtain 19.0 g of methyl 4-[(2,2-diethoxyethyl)sulfanyl]-2-fluoro-3-methoxybenzoate as an oily product.

Workup

stirringstirred at that temperature for 3 hours
customthe organic layer is separated
washThe organic layer is washed with saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent is distilled off under reduced pressure
customThe residue is purified by column chromatography (eluent: hexane-ethyl acetate=5:1)

Sources & evidence

ORD record: ord-2bfd42948f504af8b6276efad3e6f060
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06797726B1

Reaction notes

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