Sodium Bicarbonate → HCID 67107562, compound

HRID 2177835Notes

Reaction equation

HRID 2177835 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:18]Br)=[C:7]2[C:14]([O:16][CH3:17])=[O:15].[Na+].[C:21]1([S:27]([O-:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])O.[Na+]>CC(N(C)C)=O.O>[C:21]1([S:27]([CH2:18][C:6]2[CH:5]=[CH:4][C:3]3[C:8](=[C:9]([O:12][CH3:13])[CH:10]=[CH:11][C:2]=3[Br:1])[C:7]=2[C:14]([O:16][CH3:17])=[O:15])(=[O:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723840Benzenesulfinic acid, sodium saltHCID 67107945HCID 67107945, compound2×

Product 1

HCID 67107562HCID 67107562, compoundYield 28.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 5-bromo-2-bromomethyl-8-methoxynapthalene-1-carboxylate (Intermediate 189, 0.716 g), benzenesulphinic acid sodium salt (0.68 g) and sodium hydrogen carbonate (0.35 g) in DMA (15 ml) and water (3 ml) was heated at 50° C. for 2 hours. After cooling, water was added and the mixture was extracted with diethyl ether. The organic layer was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100% to give methyl 2-(benzenesulphonylmethyl)-5-bromo-8-methoxynaphthalene-1-carboxylate (0.236 g) as an oil which crystallised on standing.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-100%

Sources & evidence

ORD record
ord-c92fabdf31464e3d80f2a4c316d0ebc5
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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