Isobutyl iodide → HCID 17952293, compound

HRID 1592720Notes

Reaction equation

HRID 1592720 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].C([O-])([O-])=O.[K+].[K+].[CH2:15](I)[CH:16]([CH3:18])[CH3:17]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:15][CH:16]([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 10556Isobutyl iodideHCID 11430Potassium CarbonateHCID 805982-Bromobenzenethiol

Product 1

HCID 17952293HCID 17952293, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2-bromobenzene thiol (10.0 g, 52.8 mmol, 1.0 eq.) in DMF (250 mL) was added K2CO3 (17.5 g, 126.7 mmol, 2.4 eq.) and isobutyl iodide (7.3 mL, 63.36 mmol, 1.2 eq). The reaction was warmed to about 40° C. and stirred overnight. The mixture was diluted with EtOAc (300 mL) and washed with water (100 mL) and brine (100 mL). The organic layer was extracted with EtOAc(2×). The combined organic extracts were dried (Na2SO4), filtered and concentrated to afford 1-bromo-2-isobutylsulfanyl-benzene (12.94 g, 52.8 mmol, 100%), which is then taken to the next step without any further purification. GCMS (EI): 244.0

Workup

  1. washwashed with water (100 mL) and brine (100 mL)
  2. extractionThe organic layer was extracted with EtOAc(2×)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5b91ce23059349ed9d384ddca69787fe
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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