Boron trifluoride etherate → HCID 58340856, compound

HRID 72572Notes

Reaction equation

HRID 72572 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:26])=[C:6]([CH:25]=1)[C:7]([C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][CH2:15][N:14]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[C:13]=2[CH:24]=1)=O.B(F)(F)F.CCOCC.[SiH](CC)(CC)CC>ClCCCl.CC#N>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:26])=[C:6]([CH:25]=1)[CH2:7][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][CH2:15][N:14]([C:18](=[O:23])[C:19]([F:21])([F:22])[F:20])[C:13]=2[CH:24]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 866551971-[6-(5-Bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone

Product 1

HCID 58340856HCID 58340856, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 22402149Acetonitrile 1,2-dichloroethaneSolvent

Procedure

To a stirred solution of 1-[6-(5-bromo-2-chloro-benzoyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (36 g, 80.35 mmol) in 1,2-dichloroethane:MeCN 1:2 (180 mL) was added BF3.OEt2 (13.2 mL, 104 mmol) and Et3SiH (26.9 mL, 168.7 mmol) at 0° C. The reaction mixture was stirred overnight at room temperature then quenched by the addition of aq. NaHCO3 (˜200 mL). The resulting mixture was extracted with ethyl acetate (3×200 mL), and the combined organic layers were washed with brine (200 mL) and dried over sodium sulfate. Crude product obtained after evaporation of solvent was purified by silica gel column chromatography to furnish 1-[6-(5-bromo-2-chloro-benzyl)-2,3-dihydro-benzo[1,4]oxazin-4-yl]-2,2,2-trifluoro-ethanone (30 g).

Workup

  1. customthen quenched by the addition of aq. NaHCO3 (˜200 mL)
  2. extractionThe resulting mixture was extracted with ethyl acetate (3×200 mL)
  3. washthe combined organic layers were washed with brine (200 mL)
  4. dry with materialdried over sodium sulfate
  5. customCrude product obtained
  6. customafter evaporation of solvent
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eddbc94e7c034c62ade11f5f1b6b7749
Source dataset
uspto-grants-2014_09
Patent number
US08828951B2

Reaction notes

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