Boron trifluoride → HCID 66690841, compound

HRID 1469204Notes

Reaction equation

HRID 1469204 reaction equation
[Br:1][C:2]1[C:3]([CH3:18])=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)=O)[S:5][C:6]=1[Br:7].C([SiH](CC)CC)C.B(F)(F)F>C(Cl)Cl.CC#N>[Br:7][C:6]1[S:5][C:4]([CH2:8][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH3:17])=[CH:12][CH:11]=2)=[C:3]([CH3:18])[C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 12052TriethylsilaneHCID 66690886HCID 66690886, compound

Product 1

HCID 66690841HCID 66690841, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

To a solution of (4,5-dibromo-3-methylthiophen-2-yl)(4-ethylphenyl)methanone (54) (4.28 g, 10.6 mmole) in DCM/CH3CN (30 mL/30 mL) were added triethylsilane (5.1 mL, 31.9 mmole) and borontrifluoride diethyletherate (3.1 mL, 25.4 mmole) at 0° C. The resulting solution was stirred at ambient temperature overnight. The reaction mixture was quenched by adding MeOH (10 mL) and concentrated in vacuo. The crude residue was purified on Biotage® purification apparatus to yield the compound 55 2,3-dibromo-5-(4-ethylbenzyl)-4-methylthiophene (3.65 g, 9.76 mmole, 92%) as yellow oil.

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding MeOH (10 mL)
  3. concentrationconcentrated in vacuo
  4. customThe crude residue was purified on Biotage® purification apparatus

Sources & evidence

ORD record
ord-0c792234db074626b5ab961a3e004ea8
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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