Boron trifluoride etherate → HCID 86685118, compound

HRID 1913001Notes

Reaction equation

HRID 1913001 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:21])=[C:6]([CH: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.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>[OH-].[K+]>[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 12052TriethylsilaneHCID 86685117HCID 86685117, compound

Product 1

HCID 86685118HCID 86685118, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

(5-bromo-2-chloro-phenyl)-(4-ethoxy-2,3-difluoro-phenyl)methanol 3d (8.0 g, 21.2 mmol) was dissolved in 150 mL of mixed solution (acetonitrile and dichloromethane, v:v=2:1), followed by addition of triethylsilane (10.1 mL, 63.6 mmol) and boron trifluoride etherate (5.3 mL, 42.4 mmol). The reaction mixture was stirred for 3 hours, before 100 mL 2 M potassium hydroxide were added. The organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system C to obtain the title compound 1-[(5-bromo-2-chloro-phenyl)methyl]-4-ethoxy-2,3-difluoro-benzene 3e (5.5 g, white solid), yield: 72.4%. MS m/z (ESI): 360.5 [M+1]. 1H NMR (400 MHz, CDCl3): δ 7.36-7.27 (m, 3H), 6.81-6.76 (dd, 1H), 6.72-6.68 (dd, 1H), 4.17-4.13 (q, 2H), 4.10 (s, 2H), 1.50-1.47 (t, 3H).

Workup

  1. additionwere added
  2. extractionThe organic extract
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe resulting residue was purified by silica gel chromatography with elution system C

Sources & evidence

ORD record
ord-876d39a5a98140dc8b635a4e9ecc47ef
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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