1-Bromo-2-methylpropane → HCID 12489470, compound

HRID 132768Notes

Reaction equation

HRID 132768 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[C:7]([O:9][CH2:10][CH3:11])=[O:8].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[CH:19]([CH3:21])[CH3:20]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CN(C)C=O>[CH2:18]([C:3]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:4][CH2:5][CH2:6][C:2]1=[O:1])[CH:19]([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 69136Ethyl 2-oxocyclopentanecarboxylate

Product 1

HCID 12489470HCID 12489470, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Under vigorously agitation, 13.9 g of ethyl 2-oxocyclopentane carboxylate was added to 33.4 g of fine powdery anhydrous potassium carbonate and 1.14 g of benzyl triethyl ammonium chloride. After stirring for several minutes, to the mixture was added 60 ml of N,N-dimethyl formamide and 21.9 g of iso-butyl bromide. Upon the completion of the addition, the reaction was heated to 55° C. and allowed to continue for 6 hours with stirring. The solvent was removed under reduced pressure, and solid residue was washed with diethyl ether. The washing liquor was collected and washed with water, and removing the solvent gave a crude product. The crude product was distilled under reduced pressure, and 15.3 g of colorless liquid as a distillate cut of 139-142° C./15 mmHg was colleted. Yield: 90.0%.

Workup

  1. additionUpon the completion of the addition
  2. stirringwith stirring
  3. customThe solvent was removed under reduced pressure, and solid residue
  4. washwas washed with diethyl ether
  5. customThe washing liquor was collected
  6. washwashed with water
  7. customremoving the solvent

Sources & evidence

ORD record
ord-be753d3db2e04c4088ca05894f62a8d3
Source dataset
uspto-grants-2008_06
Patent number
US07388103B2

Reaction notes

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