3-chloro-6-(4-methoxyphenyl)pyridazine → 3-Chloro-6-(4-hydroxyphenyl)-pyridazine

HRID 1993360Notes

Reaction equation

HRID 1993360 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1>B(Br)(Br)Br.C(Cl)Cl>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 122575013-chloro-6-(4-methoxyphenyl)pyridazine

Product 1

HCID 1357417453-Chloro-6-(4-hydroxyphenyl)-pyridazine

Reagents, catalysts & solvents 1

HCID 22277759Boron tribromide dichloromethaneSolvent

Procedure

A solution of 3-chloro-6-(4-methoxy-phenyl)-pyridazine (Step 1, 2.5 g, 0.0113 mol) in 1 M BBr3/CH2Cl2 (34 mL) was stirred at RT for 16 h. The solution was concentrated in vacuo and the residue was re-dissolved in 100 mL of EtOAc. The organic phase was washed with 40 mL of water followed by 40 mL of brine, dried over Na2SO4 and concentrated in vacuo. The solid was washed with 50% EtOAc/hexane mixture to give the title compound as a yellow solid MS (ESI pos. ion) m/z: 207.2(M+H). Calc'd Exact Mass for C10H7ClN2O: 206.63.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. dissolutionthe residue was re-dissolved in 100 mL of EtOAc
  3. washThe organic phase was washed with 40 mL of water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. washThe solid was washed with 50% EtOAc/hexane mixture

Sources & evidence

ORD record
ord-4000efa6d2fb4d52a26efdd27eaab3dd
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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