1-Bromo-2-methylpropane → Methyl 4-(isobutylthio)benzoate

HRID 1908132Notes

Reaction equation

HRID 1908132 reaction equation
C([O-])([O-])=O.[K+].[K+].[SH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1.Br[CH2:19][CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[CH2:19]([S:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:16][CH:17]=1)[CH:20]([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 11430Potassium CarbonateHCID 237573Methyl 4-sulfanylbenzoate

Product 1

HCID 58551683Methyl 4-(isobutylthio)benzoateYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

K2CO3 (1.23 g, 8.92 mmol) was added to a mixture of methyl 4-sulfanylbenzoate (1.00 g, 5.95 mmol), 1-bromo-2-methyl-propane (970 μL, 8.92 mmol), and DMF (10 mL) at rt. The mixture was allowed to stir for 4 h at rt before the solids were filtered off. The solids were washed with ethyl acetate, and then were discarded. The combined filtrates were partitioned between ethyl acetate (100 mL) and water (100 mL). The layers were separated and the organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to give methyl 4-(isobutylthio)benzoate (82%) as a clear oil. ESI-MS m/z calc. 224.1. found 225.2 (M+1)+. Retention time: 1.59 minutes (3 min run).

Workup

  1. filtrationwere filtered off
  2. washThe solids were washed with ethyl acetate
  3. customThe combined filtrates were partitioned between ethyl acetate (100 mL) and water (100 mL)
  4. customThe layers were separated
  5. washthe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c9f3973db7964353a8aebfbd4f699e1c
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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