Boron trifluoride etherate → HCID 71076939, compound

HRID 576359Notes

Reaction equation

HRID 576359 reaction equation
[Br:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:5]([Cl:11])=[C:4]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][CH:15]=2)=O)[CH:3]=1.[SiH](CC)(CC)CC.B(F)(F)F.CCOCC>C(Cl)Cl.CC#N>[Br:1][C:2]1[C:7]2[S:8][CH:9]=[CH:10][C:6]=2[C:5]([Cl:11])=[C:4]([CH2:12][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH3:22])=[CH:16][CH:15]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 71110860HCID 71110860, compound

Product 1

HCID 71076939HCID 71076939, compoundYield 85.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (7-bromo-4-chlorobenzo[b]thiophen-5-yl)(4-ethoxyphenyl)methanone 98 (917 mg, 2.32 mmol) in a mixture of CH2Cl2 (9 mL) and CH3CN (30 mL) at 0° C. was added Et3SiH (1.6 mL, 9.27 mmol) and BF3.Et2O (0.47 mL, 3.48 mmol). The reaction mixture was warmed to room temperature, and then stirred overnight. The resulting solution was quenched with aqueous sat. NH4Cl solution (40 mL) and normal work-up with EtOAc was accomplished. After evaporating volatile solvents, the residue was purified by silica gel chromatography to afford the title compound (761 mg, 84%) as an off-white solid.

Workup

  1. customThe resulting solution was quenched with aqueous sat. NH4Cl solution (40 mL) and normal work-up with EtOAc
  2. customAfter evaporating volatile solvents
  3. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4258441a1e8242bfa6a96608c3293aa2
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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