Water → HCID 54241899, compound

HRID 1020459Notes

Reaction equation

HRID 1020459 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9].Br[C:11]([CH3:18])([CH3:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].C([O-])([O-])=O.[K+].[K+].O>C(Cl)(Cl)Cl>[CH3:17][C:11]([O:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[S:2][CH3:1])([CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 61261o-(Methylthio)phenol

Product 1

HCID 54241899HCID 54241899, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
105 °C

Procedure

2-Methylsulfanyl-phenol (2.00 g, 14.29 mmol), 2-bromo-2-methyl-propionic acid, ethyl ester (28 g, 142.8 mmol) and powdered K2CO3 (4.93 g, 35.7 mmol) were mixed (no solvent) and stirred at 105° C. for 8 hrs. After cooling, water and CHCl3 were added. The CHCl3 was separated, dried (MgSO4) and concentrated. Xylene was added and concentrated in vacuo (4 times) to remove the bromo ester. The resulting oil was chromatographed on silica, eluting with CH2Cl2 to obtain the title compound (2.30 g, 63% yield).

Workup

  1. temperatureAfter cooling
  2. customThe CHCl3 was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. additionXylene was added
  6. concentrationconcentrated in vacuo (4 times)
  7. customto remove the bromo ester
  8. customThe resulting oil was chromatographed on silica
  9. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-7c0fa88bc24d459995867aa190e7d7f1
Source dataset
uspto-grants-2014_05
Patent number
US08716345B2

Reaction notes

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