Hydrochloric Acid → HCID 18472282, compound

HRID 1277271Notes

Reaction equation

HRID 1277271 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=O.[SH:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[Br:1][C:2]1[CH:9]=[C:6]2[C:5](=[CH:4][CH:3]=1)[S:11][CH2:12][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 21625Ethyl 3-mercaptopropionateHCID 7363275-Bromo-2-fluorobenzaldehyde

Product 1

HCID 18472282HCID 18472282, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromo-2-fluorobenzaldehyde (0.49 g, 2.62 mmol) and ethyl 3-mercaptopropionate (0.37 ml, 2.88 mmol) in N,N-dimethylformamide (10 ml) was added potassium carbonate (0.90 g, 6.55 mmol), and the mixture was stirred at room temperature for 1 hour and then at 70° C. for 15 hours. The mixture was poured into ice-water, and made pH 4 with 1N hydrochloric acid. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with water and saturated brine, and dried with magnesium sulfate. The solvent was evaporated, and the residue was purified with silica gel column chromatography [hexane:ethyl acetate (5:1)] to give ethyl 6-bromo-2H-thiochromene-3-carboxylate (0.45 g, 58%) as yellow powder, a part of which was recrystallized from ethanol to give pale yellow needles.

Workup

  1. waitat 70° C. for 15 hours
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified with silica gel column chromatography [hexane:ethyl acetate (5:1)]

Sources & evidence

ORD record
ord-c9cea760f0894569a9794fedfb1254d2
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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