Boron Trichloride → HCID 22339619, compound

HRID 585138Notes

Reaction equation

HRID 585138 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:27]2[C:32](=[O:33])[NH:31][C:30](=[O:34])[CH:29]=[N:28]2)[CH:5]=[C:6]([CH3:26])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([C:17](=[O:25])[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH:10]=1.B(Cl)(Cl)Cl>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:27]2[C:32](=[O:33])[NH:31][C:30](=[O:34])[CH:29]=[N:28]2)[CH:5]=[C:6]([CH3:26])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([C:17](=[O:25])[C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[CH:10]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 22339496HCID 22339496, compound

Product 1

HCID 22339619HCID 22339619, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-{3-chloro-4-[3-(4-fluoro-benzoyl)-4-methoxy-phenoxy]-5-methyl-phenyl}-2H-[1,2,4]triazine-3,5-dione (1.1 g) in dichloromethane (30 mL) was added a solution of 1M boron trichloride in dichloromethane (11 mL) and the resulting suspension was stirred at ambient temperature for 4 h. Ice was added to the reaction and the resulting mixture was stirred for 30 min, extracted with ethyl acetate, the organic phase dried (Na2SO4), concentrated in vacuo and flash chromatographed on silica gel (30% THF/hexanes) to afford the title compound of Step B, 0.94 g. MS Calc.:467.8 Found:467.8.

Workup

  1. additionIce was added to the reaction
  2. stirringthe resulting mixture was stirred for 30 min
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic phase dried (Na2SO4)
  5. concentrationconcentrated in vacuo and flash
  6. customchromatographed on silica gel (30% THF/hexanes)

Sources & evidence

ORD record
ord-a6e361b41f9546eebd9e55482129aa8b
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

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