Water → HCID 54241899, compound

HRID 1788355Notes

Reaction equation

HRID 1788355 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 CHC13 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 CHC13 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-d1bf00a05ed14ec49459628116391c7d
Source dataset
uspto-grants-2009_03
Patent number
US07511175B2

Reaction notes

Loading…