Hydrogen Bromide → 2-(Tol-2-yl)-4-(Pyrid-3-yl)-1,3-Dihydroxybenzene

HRID 324935Notes

Reaction equation

HRID 324935 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([O:15]C)[C:4]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23].Br>C(O)(=O)C>[C:18]1([CH3:23])[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:4]1[C:5]([OH:15])=[C:6]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH:7]=[CH:8][C:3]=1[OH:2]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 155090961,3-Dimethoxy-2-(Tol-2-yl)-4-(Pyrid-3-yl)-Benzene

Product 1

HCID 155090972-(Tol-2-yl)-4-(Pyrid-3-yl)-1,3-DihydroxybenzeneYield 90%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1,3-Dimethoxy-2-(tol-2-yl)-4-(pyrid-3-yl)-benzene 3 (3.5 g, 11.46 mmol), acetic acid (30 ml), and hydrobromic acid (48%) (15 ml) were refluxed for 24 hr. After cooling the reaction mixture, most of the reagent was removed under reduced pressure; the residual acid was removed by mixing the concentrate with sodium bicarbonate solution (5%) (100 ml). The product was extracted into ethylacetate (100 ml), washed with water (100 ml×2) and brine (100 ml), and the ethyl acetate was evaporated. The crude product was purified by silica-gel chromatography eluting with dichloromethane and acetone (0% to 10% acetone) yielding 2.8 g (90%) of 4.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. custommost of the reagent was removed under reduced pressure
  3. customthe residual acid was removed
  4. additionby mixing the
  5. concentrationconcentrate with sodium bicarbonate solution (5%) (100 ml)
  6. extractionThe product was extracted into ethylacetate (100 ml)
  7. washwashed with water (100 ml×2) and brine (100 ml)
  8. customthe ethyl acetate was evaporated
  9. customThe crude product was purified by silica-gel chromatography
  10. washeluting with dichloromethane and acetone (0% to 10% acetone)

Sources & evidence

ORD record
ord-f0a4402d0d6c42cb9fa486a60ce2e52e
Source dataset
uspto-grants-2001_04
Patent number
US06221604B1

Reaction notes

Loading…