HCID 57445398, compound → 4-(6-Benzyl-pyridazin-3-yl)-2-fluoro-phenol

HRID 1993365Notes

Reaction equation

HRID 1993365 reaction equation
[CH2:1]([C:8]1[N:9]=[N:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20]C)=[C:16]([F:22])[CH:15]=2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>B(Br)(Br)Br.C(Cl)Cl>[CH2:1]([C:8]1[N:9]=[N:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([F:22])[CH:15]=2)=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 57445398HCID 57445398, compound

Product 1

HCID 1360707044-(6-Benzyl-pyridazin-3-yl)-2-fluoro-phenol

Reagents, catalysts & solvents 1

HCID 22277759Boron tribromide dichloromethaneSolvent

Procedure

A solution of 3-benzyl-6-(3-fluoro-4-methoxy-phenyl)-pyridazine (Step 2, 1.5 g, 5.1 mmol) in 25 mL of 1 M BBr3/CH2Cl2 was stirred at RT for 16 h. The solution was then 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 to give the title compound. The solid has poor solubility in EtOAc and CH2Cl2 and was washed with 50% EtOAc/hexane and then used in the next step (yellow solid). MS (ESI pos. ion) m/z: 281.3 (M+H). Calc'd Exact Mass for C17H13FN2O: 280.30.

Workup

  1. concentrationThe solution was then 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

Sources & evidence

ORD record
ord-f6694c79ff8a41e8b7738bd2e6628c63
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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