1-Bromo-2-methylpropane → HCID 58551683, compound

HRID 72992

Reaction equation

HRID 72992 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 58551683HCID 58551683, compoundYield 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-f5c998585a3c4560bb4a501855ae8120
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Linked notes

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