Boron Trichloride → HCID 22339619, compound

HRID 1006215Notes

Reaction equation

HRID 1006215 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-a444d2a0efde4cbdad7f080733dba96d
Source dataset
uspto-grants-2004_09
Patent number
US06787652B1

Reaction notes

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