Boron trifluoride etherate → HCID 86685118, compound

HRID 1055582Notes

Reaction equation

HRID 1055582 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:21])=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[C:12]([F:19])[C:11]=2[F:20])=O)[CH:7]=1.B(F)(F)F.CCOCC.C(=O)(O)[O-].[Na+]>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:21])=[C:6]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH3:18])=[C:12]([F:19])[C:11]=2[F:20])[CH:7]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 86685116HCID 86685116, compound

Product 1

HCID 86685118HCID 86685118, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (5-bromo-2-chloro-phenyl)-(4-ethoxy-2,3-difluoro-phenyl)methanone 23d (17.6 g, 46.8 mmol) in acetonitrile (100 mL) was added triethyl silicane (18.7 mL, 117.1 mmol) at 15° C., and then boron trifluoride diethyl ether (28.9 mL, 234.1 mmol) was added. The mixture was warmed up to room temperature and stirred for 15 hours. The reaction mixture was adjusted with saturated aqueous sodium bicarbonate to pH 7 and extracted with ethyl acetate (150 mL×3). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE to give the title compound 23e as a white solid (9.45 g, 63%). The compound was characterized by the following spectroscopic data: 1H NMR (400 MHz, CDCl3) δ(ppm): 7.34-7.30 (m, 1H), 7.29-7.26 (m, 2H), 6.79-6.75 (m, 1H), 6.71-6.66 (m, 1H), 4.12 (q, 2H), 4.04 (s, 2H), 1.47 (t, 3H).

Workup

  1. extractionextracted with ethyl acetate (150 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel chromatography
  6. washeluted with PE

Sources & evidence

ORD record
ord-81f45a4d1ab7453fac06a76d7e802615
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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