Benzophenone → HCID 58568165, compound

HRID 2193818Notes

Reaction equation

HRID 2193818 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.C([Li])CCC.[C:17]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)C>[S:4]1[CH:5]=[CH:6][C:2]([C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[OH:24])=[C:3]1[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 36136783-Bromo-2,2'-bithiopheneHCID 178418339Butyllithium

Product 1

HCID 58568165HCID 58568165, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

3-Bromo-2,2′-bithiophene (IIIa) (0.50 g, 2.04 mmol) in dry diethylether (20 mL) was added slowly to a solution of n-butyllithium (1.6 M in hexane, 1.25 mL, 2.04 mmol) in dry diethylether (20 mL) at −78° C. over 2 h under N2. The mixture was stirred for 15 minutes at the same temperature. Benzophenone (0.33 g, 1.81 mmol) was added to the mixture at −78° C., followed by stirring overnight at room temperature. The reaction was quenched with an aqueous NH4Cl-solution (2.5 M, 10 mL) and water (10 mL) at 0° C. The organic phase was separated and the aqueous phase was extracted with diethylether. The combined organic phases were washed with brine, dried over MgSO4 and evaporated under reduced pressure to give a crude oil. The oily residue was purified by column chromatography (eluent hexane/EtOAc 90:10) to afford the title compound (IIj) as a yellow oil (0.202 g, 29.0%). 1H-NMR (CDCl3): δ=7.35-7.26 (m, 10H), 7.23 (dd, J=5.1, J=1.2 Hz, 1H), 7.11 (d, J=5.4 Hz, 1H), 6.85 (dd, J=5.1, J=3.5 Hz, 1H), 6.66 (dd, J=3.5 Hz, J=1.2 Hz, 1H), 6.38 (d, J=5.4, 1H), 3.43 (br s, 1H).

Workup

  1. stirringby stirring overnight at room temperature
  2. customThe reaction was quenched with an aqueous NH4Cl-solution (2.5 M, 10 mL) and water (10 mL) at 0° C
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with diethylether
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated under reduced pressure
  8. customto give a crude oil
  9. customThe oily residue was purified by column chromatography (eluent hexane/EtOAc 90:10)

Sources & evidence

ORD record
ord-d4c72a9d18ff4025824f34cd7bc1ab74
Source dataset
uspto-grants-2012_12
Patent number
US08329923B2

Reaction notes

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