Acetone → 2-(6-Chloro-3-pyridazinylmethyl)phenol

HRID 346332Notes

Reaction equation

HRID 346332 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15]C)=[CH:4][CH:3]=1.B(Br)(Br)Br.CC(C)=O>ClCCl>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 25134Boron tribromideHCID 139582952-(6-Chloro-3-pyridazinylmethyl)anisole

Product 1

HCID 139582962-(6-Chloro-3-pyridazinylmethyl)phenolYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(6-Chloro-3-pyridazinylmethyl)anisole (prepared as described in Example 33(c)) (2.35 g) was dissolved in dry dichloromethane (20 ml) and cooled with stirring to -50°. Boron tribromide (3 ml) was then added dropwise, and the solution was allowed to warm to room temperature. After 0.5 hours the orange reaction mixture was poured into ice/water (200 ml) and acetone added to dissolve the precipitated solid. The mixture was extracted with dichloromethane, the organic extracts were separated, washed with water, dried, and evaporated. The residue was recrystallised from ethyl acetate and petroleum spirit to give 2-(6-chloro-3-pyridazinylmethyl)phenol (1.75 g, 80%), m.p. 132-132.5°.

Workup

  1. temperaturecooled
  2. additionadded
  3. dissolutionto dissolve the precipitated solid
  4. extractionThe mixture was extracted with dichloromethane
  5. customthe organic extracts were separated
  6. washwashed with water
  7. customdried
  8. customevaporated
  9. customThe residue was recrystallised from ethyl acetate and petroleum spirit

Sources & evidence

ORD record
ord-85bbea71edcb4d45aead94ccba6a151c
Source dataset
uspto-grants-1991_10
Patent number
US05061798

Reaction notes

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