1-Bromo-2-methylpropane → HCID 60167296, compound

HRID 624553Notes

Reaction equation

HRID 624553 reaction equation
[N:1]([C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]([OH:11])=[O:10])=[N+:2]=[N-:3].Br[CH2:13][CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH2:13]([O:10][C:9]([C:5]1[S:6][CH:7]=[CH:8][C:4]=1[N:1]=[N+:2]=[N-:3])=[O:11])[CH:14]([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 10796Cesium carbonateHCID 4172708HCID 4172708, compound

Product 1

HCID 60167296HCID 60167296, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Compound 13a (5.8 g, 34.3 mmol) was treated with 1-bromo-2-methylpropane (4.47 mL, 1.2 equiv.) and cesium carbonate (7.82 g, 0.7 equiv.) in anhydrous DMF (0.1 M) and heated to 80° C. for 6 h under argon. The mixture was cooled, dissolved in H2O (150 mL), and extracted with 1:1 diethyl ether:ethyl acetate (3×200 mL). The organic layer was washed with distilled H2O (5×100 mL), dried over Na2SO4, and concentrated in vacuo to give 14a as an oil (6.77 g, 77% yield).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with 1:1 diethyl ether
  3. washThe organic layer was washed with distilled H2O (5×100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34a2dbb8b30d40f1b578a3cb1c167dcc
Source dataset
uspto-grants-2016_04
Patent number
US09303042B2

Reaction notes

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