Water → HCID 19037032, compound

HRID 264861Notes

Reaction equation

HRID 264861 reaction equation
[F:1][CH2:2][C:3]1([CH3:16])[CH:8]=[CH:7][C:6]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:5]=2[O:4]1.[Br:17]Br.O>C(Cl)(Cl)Cl>[Br:17][C:7]1[C:6]2[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:5]=2[O:4][C:3]([CH2:2][F:1])([CH3:16])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 19037071HCID 19037071, compound

Product 1

HCID 19037032HCID 19037032, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 8.24 g of 2-fluoromethyl-2-methyl-6-nitro-2H-1-benzopyran dissolved in 100 ml of chloroform was added dropwise 2.7 ml of bromine with stirring under cooling with water, and the mixture was stirred for 20 hours at room temperature. After the solvent was removed, 100 ml of dioxane and 2N NaOH solution were added to the residue and stirred at room temperature for 16 hours. When ice-water was added to the reaction mixture, crystals were separated out. The crystals were collected by filtration, washed with water and dissolved in methylene chloride. It was washed with water and dried. The solvent was evaporated off to obtain 11.01 g of 4-bromo-2-fluoromethyl-2-methyl-6-nitro-2H-1-benzopyran with a melting point of 116°-117° C.

Workup

  1. stirringthe mixture was stirred for 20 hours at room temperature
  2. customAfter the solvent was removed
  3. addition100 ml of dioxane and 2N NaOH solution were added to the residue
  4. stirringstirred at room temperature for 16 hours
  5. additionWhen ice-water was added to the reaction mixture, crystals
  6. customwere separated out
  7. filtrationThe crystals were collected by filtration
  8. washwashed with water
  9. dissolutiondissolved in methylene chloride
  10. washIt was washed with water
  11. customdried
  12. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-5ef78932e25d472c8da33a116a902d3d
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

Loading…