Thiophene, 2,4-dibromo- → HCID 89525673, compound

HRID 2278352Notes

Reaction equation

HRID 2278352 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([Br:7])[CH:6]=1.[Li]CCCC.[Si:13]([O:20][CH2:21]/[CH:22]=[N:23]/[S:24]([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:25])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>CCOCC.C(Cl)Cl>[Br:7][C:5]1[CH:6]=[C:2]([CH:22]([NH:23][S:24]([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:25])[CH2:21][O:20][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14])[S:3][CH:4]=1

Participants

6

Reactant 3

HCID 2724560Thiophene, 2,4-dibromo-HCID 87221168HCID 87221168, compoundHCID 178418339Butyllithium

Product 1

HCID 89525673HCID 89525673, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

2,4-dibromothiophene (3.49 g, 14.41 mmol) was dissolved in Et2O (120 mL) at −78° C., and then n-BuLi (4.32 mL of 2.5 M, 10.8 mmol) was added dropwise and the resulting mixture was stirred for 30 minutes. This solution was cannulated into a solution of N-[(1E)-2-{[tert-butyl(dimethyl)silyl]oxy}ethylidene]-2-methylpropane-2-sulfinamide (2 g, 7.21 mmol) in 120 mL DCM at −78° C. The reaction mixture was quenched with aqueous ammonium chloride and warmed to room temperature. The mixture was extracted with ethyl acetate (3×) and the combined organic fractions were washed with brine, dried (MgSO4), and filtered. The ethyl acetate solvent was then evaporated under reduced pressure, and the resulting product purified on silica gel (EtOAc/hexanes) to give the title compound.

Workup

  1. customThe reaction mixture was quenched with aqueous ammonium chloride
  2. extractionThe mixture was extracted with ethyl acetate (3×)
  3. washthe combined organic fractions were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe ethyl acetate solvent was then evaporated under reduced pressure
  7. customthe resulting product purified on silica gel (EtOAc/hexanes)

Sources & evidence

ORD record
ord-cc094eefc2d440e9af871e70a1c277e5
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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