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

HRID 713077Notes

Reaction equation

HRID 713077 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 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (1.2 g, 8.9 mmol) was added to a mixture of methyl 4-sulfanylbenzoate (1.0 g, 6.0 mmol), 1-bromo-2-methyl-propane (1.2 g, 970 μL, 8.9 mmol), and DMF (10 mL) at room temperature. The reaction mixture was allowed to stir for 4 hours and the resulting solid was removed by filtration. The filtrate were partitioned between ethyl acetate (100 mL) and water (100 mL). The layers were separated and the organic layer was washed with brine solution, then dried over sodium sulfate, filtered and concentrated in vacuo to give methyl 4-isobutylsulfanylbenzoate (1.1 g, 83%) as a clear oil. ESI-MS m/z calc. 242.0. found 243.2 (M+1)+; Retention time: 1.73 minutes (3 min run). 1H NMR (400 MHz, CDCl3) δ 8.30 (d, J=8.3 Hz, 2H), 8.05 (d, J=8.3 Hz, 2H), 3.03 (d, J=6.5 Hz, 2H), 2.27 (dt, J=13.3, 6.6 Hz, 1H), 1.08 (d, J=6.7 Hz, 6H).

Workup

  1. customthe resulting solid was removed by filtration
  2. customThe filtrate were partitioned between ethyl acetate (100 mL) and water (100 mL)
  3. customThe layers were separated
  4. washthe organic layer was washed with brine solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7eac7b69dbc4ad093adeb26379e0d39
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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