Cesium carbonate → HCID 58136580, compound

HRID 877174Notes

Reaction equation

HRID 877174 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[OH:11].Br[C:13]([CH3:19])([CH3:18])[C:14]([O:16][CH3:17])=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)(O)[O-].[Na+]>CN(C=O)C>[CH3:18][C:13]([O:11][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=1[CH3:1])([CH3:19])[C:14]([O:16][CH3:17])=[O:15]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 795792-Methyl-3-nitrophenolHCID 90097Methyl 2-bromo-2-methylpropionate3×HCID 516892Sodium Bicarbonate

Product 1

HCID 58136580HCID 58136580, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2.00 g (13.06 mmol) of 2-methyl-3-nitrophenol were dissolved in 40 ml of DMF, and 3.55 g (19.59 mmol) of methyl 2-bromo-2-methylpropanoate and 4.68 g (14.37 mmol) of cesium carbonate were added. The reaction mixture was stirred at 100° C. for 2 d, and a further 1.77 g (9.80 mmol) of methyl 2-bromo-2-methylpropanoate were then added. The mixture was stirred at 100° C. for another 1 d, a further 1.77 g (9.80 mmol) of methyl 2-bromo-2-methylpropanoate were then added and the mixture was stirred at 100° C. for another 1 d. After cooling, saturated aqueous sodium bicarbonate solution was added and the mixture was extracted repeatedly with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate and concentrated on a rotary evaporator. The residue was purified by preparative HPLC. This gave 1.33 g (39% of theory) of the target compound.

Workup

  1. stirringThe mixture was stirred at 100° C. for another 1 d
  2. stirringthe mixture was stirred at 100° C. for another 1 d
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted repeatedly with ethyl acetate
  5. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated on a rotary evaporator
  8. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-e68f9499569d4039931299c92208cbe0
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

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