Water → HCID 19387210, compound

HRID 2399315Notes

Reaction equation

HRID 2399315 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[C:8]([CH2:13]O)=[C:7]([N:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]3=[O:21])[C:6]=2[CH:22]=1.P(Br)(Br)[Br:24].O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[C:8]([CH2:13][Br:24])=[C:7]([N:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]3=[O:21])[C:6]=2[CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 24614Phosphorus tribromideHCID 19387264HCID 19387264, compound

Product 1

HCID 19387210HCID 19387210, compoundYield 236.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-bromo-2,2-dimethyl-3-hydroxymethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran (9.0 g, 0.0248 mol) was suspended in toluene (150 ml). Phosphorus tribromide (0.94 ml, 2.69 g, 0.0099 mol) was added and the mixture heated at reflux for two hours. The cooled solution was treated with water and ethyl acetate, the organic phase separated and washed three times with aqueous sodium chloride solution, and then dried and evaporated under reduced pressure. The residue was triturated with pentane and dried to afford 9.94 g of 6-bromo-2,2-dimethyl-3-bromomethyl-4-(2-oxo-1,2-dihydropyridin-1-yl)-2H-1-benzopyran, m.p. 175° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for two hours
  3. customthe organic phase separated
  4. washwashed three times with aqueous sodium chloride solution
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue was triturated with pentane
  8. customdried

Sources & evidence

ORD record
ord-a47a4c9858564a7681f56d9ac4f5ad6b
Source dataset
uspto-grants-1995_09
Patent number
US05447943

Reaction notes

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