Boron trifluoride → 5-Bromo-3-methyl-2-(4-propylbenzyl)thiophene

HRID 1469199Notes

Reaction equation

HRID 1469199 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)=O)=[C:4]([CH3:18])[CH:3]=1.C([SiH](CC)CC)C.B(F)(F)F.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.C(#N)C>[Br:1][C:2]1[S:6][C:5]([CH2:7][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH3:17])=[CH:11][CH:10]=2)=[C:4]([CH3:18])[CH:3]=1

Participants

7

Reactant 4

HCID 6356Boron trifluorideHCID 11430Potassium CarbonateHCID 12052TriethylsilaneHCID 66691033(5-Bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanone

Product 1

HCID 666908445-Bromo-3-methyl-2-(4-propylbenzyl)thiopheneYield 94%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromo-3-methylthiophen-2-yl)(4-propylphenyl)methanone (45, 0.95 g, 2.95 mmol) in DCM (9.4 mL) and ACN (9.4 mL) was added triethylsilane (1.42 mL, 8.85 mmol) followed by BF3 etherate (1.11 mL, 8.85 mmol) under nitrogen atmosphere at 0° C. The reaction mixture was allowed warmed to room temperature and stirred for 16 hours. The mixture was poured into a saturated K2CO3 solution (50 mL) and extracted with EtOAc (100 mL). The organic phase was dried over MgSO4 and evaporated under vacuum. The residue was further purified by silica column chromatography (Biotage) to provide 5-bromo-3-methyl-2-(4-propylbenzyl)thiophene (46, 0.86 g, 2.77 mmol, 94%).

Workup

  1. extractionextracted with EtOAc (100 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. customevaporated under vacuum
  4. customThe residue was further purified by silica column chromatography (Biotage)

Sources & evidence

ORD record
ord-458f1e71c49e483896ebd871bcd45c5a
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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