Boron trifluoride etherate → HCID 84732417, compound

HRID 2277601Notes

Reaction equation

HRID 2277601 reaction equation
C([SiH](CC)CC)C.B(F)(F)F.CCOCC.[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[NH:22][C:21]2(O)[CH3:28].[Cl:30][C:31]1[CH:39]=[C:38]2[C:34]([C:35](O)([CH3:41])[NH:36][C:37]2=[O:40])=[CH:33][CH:32]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[NH:22][CH:21]2[CH3:28].[Cl:30][C:31]1[CH:39]=[C:38]2[C:34]([CH:35]([CH3:41])[NH:36][C:37]2=[O:40])=[CH:33][CH:32]=1

Participants

8

Reactant 5

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 86685928HCID 86685928, compoundHCID 86685929HCID 86685929, compound

Product 2

HCID 847324166-Chloro-2,3-dihydro-3-methyl-1H-isoindol-1-oneYield 9.6%HCID 84732417HCID 84732417, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under N2 protection, triethylsilane (23 g, 200 mmol) and trifluoroboron etherate (8.51 g, 60 mmol) were added successively at −15° C. to a mixture of 5-chloro-3-hydroxy-3-methyl-2,3-dihydro-isoindol-1-one and 6-chloro-3-hydroxy-3-methyl-2,3-dihydro-isoindol-1-one (3.95 g, 20 mmol) in dry DCM (100 mL). Afterwards, the reaction mixture was stirred at room temperature for 2 hours and a saturated aqueous solution of NaHCO3 (30 mL) was added. The mixture was then extracted with DCM and the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude mixture of products. The two regioisomers were separated by prep-HPLC to give the title compounds, 5-chloro-3-methyl-2,3-dihydro-isoindol-1-one (0.4 g, 11%) and 6-chloro-3-methyl-2,3-dihydro-isoindol-1-one (0.35 g, 9.6%) as white solids. MS: 182.0 (M+H+).

Workup

  1. extractionThe mixture was then extracted with DCM
  2. washthe organic layer was washed with brine
  3. customdried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo
  6. customto give a crude
  7. additionmixture of products
  8. customThe two regioisomers were separated by prep-HPLC

Sources & evidence

ORD record
ord-88c7f1e9b6ae42a2923650cd45745ea9
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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