Phosphate → HCID 10800903, compound

HRID 128836Notes

Reaction equation

HRID 128836 reaction equation
[Br:1][C:2]1[N:3]([CH3:13])[C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.CC(=CC)C.Cl([O-])=[O:20].[Na+].Cl([O-])=O.P([O-])([O-])([O-])=O>O.CC(O)C.O1CCOCC1>[Br:1][C:2]1[N:3]([CH3:13])[C:4]2[C:9]([C:10]=1[C:11]([OH:20])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

9

Reactant 5

HCID 1061PhosphateHCID 105532-Methyl-2-buteneHCID 197148ChloriteHCID 329917HCID 329917, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 10800903HCID 10800903, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
25 °C

Procedure

To a vigorously stirred solution of 2.38 g (10 mmol) of 2-bromo-1-methylindole-3-carboxaldehyde [XXVI: R1 =H, R3 =CH3, X=Br], 10 mL of 2-methyl-2-butene, and 40 mL of p-dioxane at 25° C. was added dropwise over ca. 15 minutes a solution of 5 g (55 mmol) of sodium chlorite and 5 g (36 mmol) of NaH2PO4.H2O in 25 mL of water. The solution was maintained at 25° C. After 3.5 hours, the mixture was treated with an additional 2.5 g each of the chlorite and phosphate. After a total reaction time of 24 hours, the mixture was extracted 3 times with dichloromethane, then the aqueous phase was acidified to pH 2 with aqueous HCl, and extracted once more. The combined organic extracts were washed with water, dried, and evaporated to leave a solid residue that was boiled in 2 -propanol. After cooling, the solids were collected by filtration, washed with a little 2-propanol, and dried to leave 2.21 g (87%) of 2-bromo-1-methylindole-3-carboxylic acid [XXVII: R1 =H, R3 =CH3, X=Br] as a beige solid; mp ca. 198° C. (dec), in 2 crops.

Workup

  1. extractionAfter a total reaction time of 24 hours, the mixture was extracted 3 times with dichloromethane
  2. extractionextracted once more
  3. washThe combined organic extracts were washed with water
  4. customdried
  5. customevaporated
  6. customto leave a solid residue that
  7. temperatureAfter cooling
  8. filtrationthe solids were collected by filtration
  9. washwashed with a little 2-propanol
  10. customdried

Sources & evidence

ORD record
ord-1fc627fc0d30491ca81224c87a3695c5
Source dataset
uspto-grants-1995_11
Patent number
US05464861

Reaction notes

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