Phosphate → HCID 19801176, compound

HRID 1646600Notes

Reaction equation

HRID 1646600 reaction equation
P([O-])([O-])([O-])=O.[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH2:9][CH:10]=[CH:11]2.ClC1C=CC=C(C(OO)=[O:24])C=1>C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl>[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[C:10]1[O:24][CH:11]12

Participants

6

Reactant 3

HCID 1061PhosphateHCID 70297m-Chloroperbenzoic acid3×HCID 133302097-Bromo-1H-indene

Product 1

HCID 19801176HCID 19801176, compoundYield 38.4%

Reagents, catalysts & solvents 2

HCID 16028TetrabutylammoniumCatalystHCID 6344DichloromethaneSolvent

Procedure

250 ml of pH 8 phosphate buffer, 150 ml of methylene chloride, 200 mg of tetrabutylammonium hydrogenosulphate and 10 g of 4-bromo-3H-indene are mixed together. At 0° C. 10 g of metachloroperbenzoic acid is added in several lots, then the temperature of the mixture is allowed to rise to the ambient over 4 hours, 10 g of metachloroperbenzoic acid is added at 0° C. and the temperature is allowed to rise to 20° C. over 2 hours. 3 g of metachloroperbenzoic acid is added and the mixture is left for 16 hours at ambient temperature, then decanted and extracted with methylene chloride; the extracts are washed with water, with a thiosulphate solution and with water, dried and evaporated to dryness. The residue is chromatographed on silica, eluting with a mixture of hexane and isopropyl ether (9-1) with 3% of triethylamine, and 4.11 g of expected product is isolated.

Workup

  1. customAt 0° C
  2. waitto rise to 20° C. over 2 hours
  3. waitthe mixture is left for 16 hours at ambient temperature
  4. customdecanted
  5. extractionextracted with methylene chloride
  6. washthe extracts are washed with water, with a thiosulphate solution and with water
  7. customdried
  8. customevaporated to dryness
  9. customThe residue is chromatographed on silica
  10. washeluting with a mixture of hexane and isopropyl ether (9-1) with 3% of triethylamine

Sources & evidence

ORD record
ord-63ebc2673cfe46afad592e986877acab
Source dataset
uspto-grants-1993_01
Patent number
US05180741

Reaction notes

Loading…