2,4,6-Trimethylpyridine → 3-(3-Bromophenyl)cyclobutan-1-one

HRID 2280854Notes

Reaction equation

HRID 2280854 reaction equation
CN(C)[C:3](=[O:5])[CH3:4].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[Br:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=[CH2:30])[CH:24]=1.N1C(C)=CC(C)=CC=1C>ClCCCl>[Br:22][C:23]1[CH:24]=[C:25]([CH:29]2[CH2:30][C:3](=[O:5])[CH2:4]2)[CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 31374DimethylacetamideHCID 67749Trifluoromethanesulfonic anhydrideHCID 748703-Bromostyrene

Product 1

HCID 177501013-(3-Bromophenyl)cyclobutan-1-oneYield 27.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

N,N-Dimethylacetamide (9.0 g, 103 mmol) was dissolved in 1,2-dichloroethane (200 mL). The solution was cooled to 0° C. before trifluoromethanesulfonic anhydride (63 g, 223 mmol) was added. The reaction was stirred for an additional 60 min at 0° C. Then 1-bromo-3-vinylbenzene (15 g, 81.9 mmol) and 2,4,6-collidine (10.5 g, 86.6 mmol) were added. The reaction was heated to reflux overnight, quenched by addition of water (300 mL) and stirred for 2 hr at rt. The mixture was extracted with DCM (300 mL×3). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. Purification by CC (EA/PE=1:20) gave the title compound 2a (5.0 g, 27%) as a pale yellow solid.

Workup

  1. additionwas added
  2. temperatureThe reaction was heated
  3. temperatureto reflux overnight
  4. customquenched by addition of water (300 mL)
  5. stirringstirred for 2 hr at rt
  6. extractionThe mixture was extracted with DCM (300 mL×3)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customPurification by CC (EA/PE=1:20)

Sources & evidence

ORD record
ord-b98b542fd5a74bd69e86d1abaa11089e
Source dataset
uspto-grants-2015_09
Patent number
US09139539B2

Reaction notes

Loading…