1-Bromo-2-methylpropane → HCID 25212074, compound

HRID 1774306Notes

Reaction equation

HRID 1774306 reaction equation
C(OC([NH:8][CH:9]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH3:27])[CH:19]=1)[CH2:10][C:11](=[O:17])[CH2:12][C:13]([O:15]C)=O)=O)(C)(C)C.C([O-])([O-])=O.[K+].[K+].[CH2:34](Br)[CH:35]([CH3:37])[CH3:36]>CC(C)=O.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH3:27][O:26][C:20]1[CH:19]=[C:18]([CH:9]2[NH:10][C:11](=[O:17])[CH:12]=[C:13]([O:15][CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:8]2)[CH:23]=[CH:22][C:21]=1[O:24][CH3:25]

Participants

6

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 58531816HCID 58531816, compound

Product 1

HCID 25212074HCID 25212074, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

With reference to Scheme 1, compound 4 (0.5 g, 1.3 mmol) and K2CO3 (0.5 g) was suspended in acetone (10 ml) followed by addition of TBAI (50 mg). To this mixture, isobutyl bromide (0.3 ml, 2.8 mmol) was added slowly. The reaction was refluxed for 3 h and quenched with water (50 ml). The aqueous phase was extracted with ethyl acetate (20 ml) twice. The combined organics was washed with brine and dried over sodium sulfate. Removal of the solvent gave a yellow oil residue, which was purified by chromatography on silica gel (elute with CH2Cl2/EtOAc 1:1) to give a mixture of compound 5 and 6 as light yellow oil (0.45 g, 78%).

Workup

  1. temperatureThe reaction was refluxed for 3 h
  2. customquenched with water (50 ml)
  3. extractionThe aqueous phase was extracted with ethyl acetate (20 ml) twice
  4. washThe combined organics was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customRemoval of the solvent
  7. customgave a yellow oil residue, which
  8. customwas purified by chromatography on silica gel (elute with CH2Cl2/EtOAc 1:1)
  9. customto give

Sources & evidence

ORD record
ord-b39289a7c0ec44fb970c39b73473cb0c
Source dataset
uspto-grants-2016_02
Patent number
US09260391B2

Reaction notes

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